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Recent advances in the catalytic cyclopropanation of unsaturated compounds with diazomethane

Leonid Gennad'evich Menchikov 1
Leonid Gennad'evich Menchikov
, 
Evgenii Vladimirovich Shulishov 1
Evgenii Vladimirovich Shulishov
, 
1 N.D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow
10.1070/RCR4982
Published 30 November 2020
Review , RCR4982, Volume 90, Issue 2, 199-230
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Menchikov L. G., Shulishov E. V., Tomilov Y. V. Recent advances in the catalytic cyclopropanation of unsaturated compounds with diazomethane // Russian Chemical Reviews. 2020. Vol. 90. No. 2. pp. 199-230.
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Menchikov L. G., Shulishov E. V., Tomilov Y. V. Recent advances in the catalytic cyclopropanation of unsaturated compounds with diazomethane // Russian Chemical Reviews. 2020. Vol. 90. No. 2. pp. 199-230.
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TY - JOUR
DO - 10.1070/RCR4982
UR - https://rcr.colab.ws/publications/10.1070/RCR4982
TI - Recent advances in the catalytic cyclopropanation of unsaturated compounds with diazomethane
T2 - Russian Chemical Reviews
AU - Menchikov, Leonid Gennad'evich
AU - Shulishov, Evgenii Vladimirovich
AU - Tomilov, Yury Vasil'evich
PY - 2020
DA - 2020/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 199-230
IS - 2
VL - 90
ER -
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@article{2020_Menchikov,
author = {Leonid Gennad'evich Menchikov and Evgenii Vladimirovich Shulishov and Yury Vasil'evich Tomilov},
title = {Recent advances in the catalytic cyclopropanation of unsaturated compounds with diazomethane},
journal = {Russian Chemical Reviews},
year = {2020},
volume = {90},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4982},
number = {2},
pages = {199--230},
doi = {10.1070/RCR4982}
}
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Menchikov, Leonid Gennad'evich, et al. “Recent advances in the catalytic cyclopropanation of unsaturated compounds with diazomethane.” Russian Chemical Reviews, vol. 90, no. 2, Nov. 2020, pp. 199-230. https://rcr.colab.ws/publications/10.1070/RCR4982.
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Keywords

catalyst
compound
cyclopropanation
diazomethane
generation
iron-catalyzed
palladium
unsaturated

Abstract

The main achievements and development trends of the past 107--15 years related to the catalytic cyclopropanation of unsaturated compounds with diazomethane are integrated and analyzed. The attention is focused on the most efficient catalysts based on palladium compounds. Data on the effects of substrate structure and nature of catalyst components on the regio- and stereoselectivity of these reactions are systematized. Characteristic features of safe methods for diazomethane generation are considered, including the use of membrane technologies and continuous-flow and \emph{in situ} preparation methods, which have prospects for industrial application.

The bibliography includes 281 references.

References

1.
rcr_90_2_199bib1
Kulinkovich
2015
3.
rcr_90_2_199bib3
Pellissier
2009
4.
rcr_90_2_199bib4
Breitmaier
2006
5.
rcr_90_2_199bib5
Matsumura
2013
6.
rcr_90_2_199bib6
Crombie
1961
9.
Natural Compounds Containing a Condensed Cyclopropane Ring. Natural and Synthetic Aspects
Keglevich P., Keglevich A., Hazai L., Kalaus G., Szantay C.
Current Organic Chemistry , 2014
10.
Diterpenes and a lignan from Jatropha grossidentata
Schmeda-Hirschmann G., Tsichritzis F., Jakupovic J.
Phytochemistry , 1992
12.
rcr_90_2_199bib12
Salaün
2000
13.
rcr_90_2_199bib13
Rappoport
1987
14.
Arlt D., Jautelat M., Lantzsch R.
1981
15.
rcr_90_2_199bib15
Katsuda
2012
17.
rcr_90_2_199bib17
de Meijere
2000
19.
Biosynthesis and metabolism of cyclopropane rings in natural compounds.
Wessjohann L.A., Brandt W., Thiemann T.
Chemical Reviews , 2003
21.
Biosynthesis of cyclopropane rings
Law J.H.
Accounts of Chemical Research , 1971
22.
Enzymatic Chemistry of Cyclopropane, Epoxide, and Aziridine Biosynthesis
Thibodeaux C.J., Chang W., Liu H.
Chemical Reviews , 2011
23.
The Activity of Escherichia coli Cyclopropane Fatty Acid Synthase Depends on the Presence of Bicarbonate
Iwig D.F., Uchida A., Stromberg J.A., Booker S.J.
Journal of the American Chemical Society , 2005
24.
The biosynthesis of steroids and triterpenoids
D. Brown G.
Natural Product Reports , 1998
25.
The biosynthesis of marine natural products
Garson M.J.
Chemical Reviews , 1993
28.
Recent advances in the total synthesis of cyclopropane-containing natural products.
Chen D.Y., Pouwer R.H., Richard J.
Chemical Society Reviews , 2012
29.
Cyclopropanation Strategies in Recent Total Syntheses
Ebner C., Carreira E.M.
Chemical Reviews , 2017
30.
Methods for the synthesis of donor-acceptor cyclopropanes
Tomilov Y.V., Menchikov L.G., Novikov R.A., Ivanova O.A., Trushkov I.V.
Russian Chemical Reviews , 2018
31.
rcr_90_2_199bib31
de Meijere
Sci. Synth. , 2009
32.
rcr_90_2_199bib32
Roy
2011
33.
Catalytic decomposition of diazomethane as a general method for the methylenation of chemical compounds
Tomilov Y.V., Dokitchev V.A., Dzhemilev U.M., Nefedov O.M.
Russian Chemical Reviews , 1993
34.
rcr_90_2_199bib34
Zollinger
1995
35.
rcr_90_2_199bib35
Zollinger
1994
36.
rcr_90_2_199bib36
Regitz
1986
37.
Developments in the chemistry of diazo-alkanes
Cowell G.W., Ledwith A.
Quarterly Reviews Chemical Society , 1970
38.
rcr_90_2_199bib38
de Boer
Org. Synth. Collec. , 1963
40.
The reagent Et2AlX/CH2N2 in cyclopropanation of sterically hindered olefins, as well as oxygen- and nitrogen-containing unsaturated compounds
Ramazanov I.R., Yaroslavova A.V., Yaubasarov N.R., Gil’manova E.N., Dzhemilev U.M.
Russian Chemical Bulletin , 2019
41.
Three-Membered-Ring-Based Molecular Architectures
de Meijere A., Kozhushkov S.I., Schill H.
Chemical Reviews , 2006
42.
Recent Developments in Pd‐Catalyzed Reactions of Diazo Compounds
Zhang Y., Wang J.
European Journal of Organic Chemistry , 2011
43.
Metal Complex Catalysis in the Synthesis of Spirocarbocycles
D’yakonov V.A., Trapeznikova O.A., de Meijere A., Dzhemilev U.M.
Chemical Reviews , 2014
44.
rcr_90_2_199bib44
de Meijere
2002
46.
One Pot, Two Phases: Iron-Catalyzed Cyclopropanation with In Situ Generated Diazomethane
Kaschel J., Schneider T.F., Werz D.B.
Angewandte Chemie - International Edition , 2012
47.
Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations
Svec R.L., Hergenrother P.J.
Angewandte Chemie - International Edition , 2020
48.
rcr_90_2_199bib48
Pellissier
2017
49.
Stereoselective Cyclopropanation Reactions
Lebel H., Marcoux J., Molinaro C., Charette A.B.
Chemical Reviews , 2003
50.
Asymmetric Cyclopropanation Reactions
Dalpozzo R., Bartoli G., Bencivenni G.
Synthesis , 2014
51.
Ueber Diazomethan
Pechmann H.V.
Berichte der deutschen chemischen Gesellschaft , 1894
53.
rcr_90_2_199bib53
Arndt
Org. Synth. Collect. , 1943
54.
Catalytic cyclopropanation of spiro[2.4]hepta-4,6-diene with diazomethane
Shulishov E.V., Pantyukh O.A., Menchikov L.G., Tomilov Y.V.
Tetrahedron Letters , 2019
55.
Development of a Continuous Process for the Industrial Generation of Diazomethane1
Proctor L.D., Warr A.J.
Organic Process Research and Development , 2002
57.
DIAZOMETHANE
Organic Syntheses , 1961
58.
Nefedov Oleg Matveevich, Tomilov Yury Vasil'evich, Kostitsyn Andrei B, Dzhemilev Usein Memetovich, Dokitchev Vladimir Anatol'evich
Mendeleev Communications , 1992
60.
Reactions of diazoalkanes with unsaturated compounds 8. Catalytic cyclopropanation of allyl alcohols and allylamines with diazomethane
Tomilov Y.V., Kostitsyn A.B., Dokichev V.A., Dzhemilev U.M., Nefedov O.M.
Russian Chemical Bulletin , 1989
61.
rcr_90_2_199bib61
Shulishov
Chemistry Select , 2020
64.
Automated library synthesis of cyclopropyl boronic esters employing diazomethane in a tube-in-tube flow reactor
Koolman H.F., Kantor S., Bogdan A.R., Wang Y., Pan J.Y., Djuric S.W.
Organic and Biomolecular Chemistry , 2016
65.
On-Demand Generation and Consumption of Diazomethane in Multistep Continuous Flow Systems
Yang H., Martin B., Schenkel B.
Organic Process Research and Development , 2018
66.
Taming hazardous chemistry by continuous flow technology
Movsisyan M., Delbeke E.I., Berton J.K., Battilocchio C., Ley S.V., Stevens C.V.
Chemical Society Reviews , 2016
69.
Scalable in Situ Diazomethane Generation in Continuous-Flow Reactors
Rossi E., Woehl P., Maggini M.
Organic Process Research and Development , 2011
70.
The Generation of Diazo Compounds in Continuous‐Flow
Hock K.J., Koenigs R.M.
Chemistry - A European Journal , 2018
71.
rcr_90_2_199bib71
72.
rcr_90_2_199bib72
Archibald
Chimica Oggi , 2000
73.
rcr_90_2_199bib73
74.
rcr_90_2_199bib74
76.
rcr_90_2_199bib76
Li
J. Am. Chem. Soc. , 2002
77.
Asymmetric Inter- and Intramolecular Cyclopropanation of Alkenes Catalyzed by Chiral Ruthenium Porphyrins. Synthesis and Crystal Structure of a Chiral Metalloporphyrin Carbene Complex
Che C., Huang J., Lee F., Li Y., Lai T., Kwong H., Teng P., Lee W., Lo W., Peng S., Zhou Z.
Journal of the American Chemical Society , 2001
78.
rcr_90_2_199bib78
Dai
J. Am. Chem. Soc. , 2004
80.
Mechanism of copper(I)-catalyzed cyclopropanation: a DFT study calibrated with copper(I) alkene complexes
Straub B.F., Gruber I., Rominger F., Hofmann P.
Journal of Organometallic Chemistry , 2003
81.
Palladium-Catalyzed Cyclopropanation of Alkenyl Silanes by Diazoalkanes: Evidence for a Pd0Mechanism
Berthon-Gelloz G., Marchant M., Straub B., Marko I.
Chemistry - A European Journal , 2009
82.
10.1021/ja027762+
84.
Cyclopropanation of Cyclohexenone by Diazomethane Catalyzed by Palladium Diacetate:  Evidence for the Formation of Palladium(0) Nanoparticles
Illa O., Rodríguez-García C., Acosta-Silva C., Favier I., Picurelli D., Oliva A., Gómez M., Branchadell V., Ortuño R.M.
Organometallics , 2007
85.
Reactions of diazoalkanes with unsaturated compounds
Dzhemilev U.M., Dokichev V.A., Sultanov S.Z., Khusnutdinov R.I., Tomilov Y.V., Nefedov O.M., Tolstikov G.A.
Russian Chemical Bulletin , 1989
86.
Shulishov Evgenii Vladimirovich, Pantyukh Olga Aleksandrovna, Menchikov Leonid Gennad'evich, Tomilov Yury Vasil'evich
Mendeleev Communications , 2020
87.
Reaction of diazoalkanes with unsaturated compounds. 11. Relative reactivity of olefins on catalytic cyclopropanation with diazomethane and palladium catalysts
Dzhemilev U.M., Dokichev V.A., Sultanov S.Z., Khursan S.L., Nefedov O.M., Tomilov Y.V., Kostitsyn A.B.
Russian Chemical Bulletin , 1992
88.
Interaction of diazoalkanes with unsaturated compounds
Dzhemilev U.M., Dokichev V.A., Maidanova I.O., Nefedov O.M., Tomilov Y.V.
Russian Chemical Bulletin , 1993
89.
Exceptional reactivity of the bicyclo[2.2.1]heptene double bond
Huisgen R., Ooms P.H., Mingin M., Allinger N.L.
Journal of the American Chemical Society , 1980
90.
The norbornene mystery revealed
Steinmann S.N., Vogel P., Mo Y., Corminboeuf C.
Chemical Communications , 2011
93.
Cyclopropanation of Carbon-Carbon Double Bonds in Ring D of Ergot Alkaloids
Szántay C., Hajós G., Incze M., Dörnyei G., Kovács P., Egyed O.
Heterocycles , 2013
94.
The First Enantiomerically Pure [n]Triangulanes and Analogues: σ-[n]Helicenes with Remarkable Features
de Meijere A., Khlebnikov A.F., Kozhushkov S.I., Kostikov R.R., Schreiner P.R., Wittkopp A., Rinderspacher C., Menzel H., Yufit D.S., Howard J.A.
Chemistry - A European Journal , 2002
95.
A Convergent Route to Enantiomerically Pure Higher [n?2]Triangulanedimethanol Derivatives and [n]Triangulanes (n?7)
de Meijere A., Khlebnikov A.F., Kozhushkov S.I., Miyazawa K., Frank D., Schreiner P.R., Rinderspacher B.C., Yufit D.S., Howard J.A.
Angewandte Chemie - International Edition , 2004
96.
High Energy Fuels II: Gas Chromatographic Separation of Energetic Compounds Derived from Dicyclopentadiene
Lin Y., Linc C., Liou K., Cheng S., Chang M.
Journal of the Chinese Chemical Society , 1986
97.
rcr_90_2_199bib97
Molchanov
Zh. Org. Khim. , 1991
98.
rcr_90_2_199bib98
Molchanov
ChemInform , 1992
99.
Conformational Dynamics of Tetraisopropylmethane and of Tetracyclopropylmethane1
Anderson J.E., de Meijere A., Kozhushkov S.I., Lunazzi L., Mazzanti A.
Journal of the American Chemical Society , 2002
100.
Tetracyclopropylmethane: A Unique Hydrocarbon with S4 Symmetry
Kozhushkov S.I., Kostikov R.R., Molchanov A.P., Boese R., Benet-Buchholz J., Schreiner P.R., Rinderspacher C., Ghiviriga I., de Meijere A.
Angewandte Chemie - International Edition , 2001
101.
rcr_90_2_199bib101
Ramana
2002
102.
rcr_90_2_199bib102
Kozhushkov
2005
103.
Synthesis of Pseudomonas quorum-sensing autoinducer analogs and structural entities required for induction of apoptosis in macrophages
Horikawa M., Tateda K., Tuzuki E., Ishii Y., Ueda C., Takabatake T., Miyairi S., Yamaguchi K., Ishiguro M.
Bioorganic and Medicinal Chemistry Letters , 2006
104.
4-Amino-2-alkyl-butyramides as small molecule CCR2 antagonists with favorable pharmacokinetic properties
Butora G., Morriello G.J., Kothandaraman S., Guiadeen D., Pasternak A., Parsons W.H., MacCoss M., Vicario P.P., Cascieri M.A., Yang L.
Bioorganic and Medicinal Chemistry Letters , 2006
105.
Reactions of diazoalkanes with unsaturated compounds 16. Catalytic reactions of diazomethane with 2-alkenyl-1,3-oxazolidines and 2-alkenyl-1,3-oxathiolanes
Khanova M.D., Sultanova R.M., Rafikov R.R., Baykova I.P., Biglova R.Z., Dokichev V.A., Tomilov Y.V.
Russian Chemical Bulletin , 2008
106.
Cyclizations of 5-Hexenyl, 6-Heptenyl, 7-Octenyl, and 8-Nonenyl Radicals. The Kinetic and Regiochemical Impact of Fluorine and Oxygen Substituents
Li A., Shtarev A.B., Smart B.E., Yang Z., Lusztyk J., Ingold K.U., Bravo A., Dolbier W.R.
Journal of Organic Chemistry , 1999
107.
Bis(gem-dihalocyclopropanes): synthesis and heterocyclization upon treatment with nitronium triflate
Sedenkov K.N., Averin E.B., Grishin Y.K., Kuznetsova T.S., Zefirov N.S.
Russian Chemical Bulletin , 2016
109.
1-Alkyl-4-phenyl-6-alkoxy-1H-quinazolin-2-ones: A Novel Series of Potent Calcium-Sensing Receptor Antagonists
Widler L., Altmann E., Beerli R., Breitenstein W., Bouhelal R., Buhl T., Gamse R., Gerspacher M., Halleux C., John M.R., Lehmann H., Kalb O., Kneissel M., Missbach M., Müller I.R., et. al.
Journal of Medicinal Chemistry , 2010
110.
Macrocyclic piperazinones as potent dual inhibitors of farnesyltransferase and geranylgeranyltransferase-I
Dinsmore C.J., Zartman C.B., Bergman J.M., Abrams M.T., Buser C.A., Culberson J.C., Davide J.P., Ellis-Hutchings M., Fernandes C., Graham S.L., Hartman G.D., Huber H.E., Lobell R.B., Mosser S.D., Robinson R.G., et. al.
Bioorganic and Medicinal Chemistry Letters , 2004
111.
rcr_90_2_199bib111
Ptashko
Bash. Khim. Zh. , 2011
112.
rcr_90_2_199bib112
Christoffers
2006
113.
1-Allylgermatrane. Synthesis, Structure and Reaction with Diazomethane
Zaitseva G.S., Karlov S.S., Alekseyeva E.S., Aslanov L.A., Avtomonov E.V., Lorberth J.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences , 1997
114.
Dual Metalloprotease Inhibitors. 6. Incorporation of Bicyclic and Substituted Monocyclic Azepinones as Dipeptide Surrogates in Angiotensin-Converting Enzyme/Neutral Endopeptidase Inhibitors
Robl J.A., Cimarusti M.P., Simpkins L.M., Brown B., Ryono D.E., Bird J.E., Asaad M.M., Schaeffer T.R., Trippodo N.C.
Journal of Medicinal Chemistry , 1996
115.
Hepatitis C virus NS3-4A serine protease inhibitors: Use of a P2–P1 cyclopropyl alanine combination for improved potency
Bogen S., Saksena A.K., Arasappan A., Gu H., Njoroge F.G., Girijavallabhan V., Pichardo J., Butkiewicz N., Prongay A., Madison V.
Bioorganic and Medicinal Chemistry Letters , 2005
116.
Inhibitors of HCV NS5B polymerase: Synthesis and structure–activity relationships of unsymmetrical 1-hydroxy-4,4-dialkyl-3-oxo-3,4-dihydronaphthalene benzothiadiazine derivatives
Krueger A.C., Madigan D.L., Green B.E., Hutchinson D.K., Jiang W.W., Kati W.M., Liu Y., Maring C.J., Masse S.V., McDaniel K.F., Middleton T.R., Mo H., Molla A., Montgomery D.A., Ng T.I., et. al.
Bioorganic and Medicinal Chemistry Letters , 2007
118.
Stereodivergent Synthesis of α,α-Disubstituted α-Amino Acids via Synergistic Cu/Ir Catalysis
Wei L., Zhu Q., Xu S., Chang X., Wang C.
Journal of the American Chemical Society , 2018
119.
rcr_90_2_199bib119
Morimoto
2002
120.
rcr_90_2_199bib120
Hallinan
1994
121.
Interactions of Isopenicillin N Synthase with Cyclopropyl-Containing Substrate Analogues Reveal New Mechanistic Insight,
Howard-Jones A.R., Elkins J.M., Clifton I.J., Roach P.L., Adlington R.M., Baldwin J.E., Rutledge P.J.
Biochemistry , 2007
122.
Synthesis of (S)-α-Cyclopropyl-4- phosphonophenylglycine
Ma D., Zhu W.
Journal of Organic Chemistry , 2000
123.
A New Method for the Synthesis of Chiral β-Branched α-Amino Acids
Spangenberg T., Schoenfelder A., Breit B., Mann A.
Organic Letters , 2007
124.
1,2-Diastereoselective C-C Bond-Forming Reactions for the Synthesis of Chiral β-Branched α-Amino Acids
Spangenberg T., Schoenfelder A., Breit B., Mann A.
European Journal of Organic Chemistry , 2010
126.
Discovery of a Potent Acyclic, Tripeptidic, Acyl Sulfonamide Inhibitor of Hepatitis C Virus NS3 Protease as a Back-up to Asunaprevir with the Potential for Once-Daily Dosing
Sun L., Mull E., Zheng B., D’Andrea S., Zhao Q., Wang A.X., Sin N., Venables B.L., Sit S., Chen Y., Chen J., Cocuzza A., Bilder D.M., Mathur A., Rampulla R., et. al.
Journal of Medicinal Chemistry , 2016
127.
Potent tricyclic pyrazole tetrazole agonists of the nicotinic acid receptor (GPR109a)
Boatman P.D., Schrader T.O., Kasem M., Johnson B.R., Skinner P.J., Jung J., Xu J., Cherrier M.C., Webb P.J., Semple G., Sage C.R., Knudsen J., Chen R., Taggart A.K., Carballo-Jane E., et. al.
Bioorganic and Medicinal Chemistry Letters , 2010
128.
(1aR,5aR)1a,3,5,5a-Tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic Acid (MK-1903): A Potent GPR109a Agonist that Lowers Free Fatty Acids in Humans
Boatman P.D., Lauring B., Schrader T.O., Kasem M., Johnson B.R., Skinner P., Jung J., Xu J., Cherrier M.C., Webb P.J., Semple G., Sage C.R., Knudsen J., Chen R., Luo W., et. al.
Journal of Medicinal Chemistry , 2012
130.
Optimization of LpxC Inhibitors for Antibacterial Activity and Cardiovascular Safety
Cohen F., Aggen J.B., Andrews L.D., Assar Z., Boggs J., Choi T., Dozzo P., Easterday A.N., Haglund C.M., Hildebrandt D.J., Holt M.C., Joly K., Jubb A., Kamal Z., Kane T.R., et. al.
ChemMedChem , 2019
131.
Design, synthesis, and structure–activity relationship of novel CCR2 antagonists
Kothandaraman S., Donnely K.L., Butora G., Jiao R., Pasternak A., Morriello G.J., Goble S.D., Zhou C., Mills S.G., MacCoss M., Vicario P.P., Ayala J.M., DeMartino J.A., Struthers M., Cascieri M.A., et. al.
Bioorganic and Medicinal Chemistry Letters , 2009
133.
Discovery of 4′-Chloromethyl-2′-deoxy-3′,5′-di-O-isobutyryl-2′-fluorocytidine (ALS-8176), A First-in-Class RSV Polymerase Inhibitor for Treatment of Human Respiratory Syncytial Virus Infection
Wang G., Deval J., Hong J., Dyatkina N., Prhavc M., Taylor J., Fung A., Jin Z., Stevens S.K., Serebryany V., Liu J., Zhang Q., Tam Y., Chanda S.M., Smith D.B., et. al.
Journal of Medicinal Chemistry , 2015
134.
rcr_90_2_199bib134
135.
rcr_90_2_199bib135
138.
rcr_90_2_199bib138
Tang
Tetrahedron , 2004
139.
Laboratory-Scale Membrane Reactor for the Generation of Anhydrous Diazomethane
Dallinger D., Pinho V.D., Gutmann B., Kappe C.O.
Journal of Organic Chemistry , 2016
140.
Transition metal catalysed cyclopropanation of olefin
Paulissen R., Hubert A.J., Teyssie P.
Tetrahedron Letters , 1972
141.
Tomilova Larisa Godvigovna, Ivanov Alexey V, Kostyuchenko Irina Viktorovna, Shulishov Evgenii Vladimirovich, Nefedov Oleg Matveevich
Mendeleev Communications , 2002
142.
Discovery of Vilaprisan (BAY 1002670): A Highly Potent and Selective Progesterone Receptor Modulator Optimized for Gynecologic Therapies
Möller C., Bone W., Cleve A., Klar U., Rotgeri A., Rottmann A., Schultze‐Mosgau M., Wagenfeld A., Schwede W.
ChemMedChem , 2018
144.
Design, optimization, and in vivo evaluation of a series of pyridine derivatives with dual NK1 antagonism and SERT inhibition for the treatment of depression
Gillman K.W., Parker M.F., Silva M., Degnan A.P., Tora G.O., Lodge N.J., Li Y., Lelas S., Taber M., Krause R.G., Bertekap R.L., Newton A.E., Pieschl R.L., Lengyel K.D., Johnson K.A., et. al.
Bioorganic and Medicinal Chemistry Letters , 2013
145.
Discovery of Potent Orally Active Thrombin Receptor (Protease Activated Receptor 1) Antagonists as Novel Antithrombotic Agents
Chackalamannil S., Xia Y., Greenlee W.J., Clasby M., Doller D., Tsai H., Asberom T., Czarniecki M., Ahn H., Boykow G., Foster C., Agans-Fantuzzi J., Bryant M., Lau J., Chintala M., et. al.
Journal of Medicinal Chemistry , 2005
146.
The First Enantiomerically Pure Triangulane (M)-Trispiro[2.0.0.2.1.1]nonane Is a σ-[4]Helicene
de Meijere A., Khlebnikov A.F., Kostikov R.R., Kozhushkov S.I., Schreiner P.R., Wittkopp A., Yufit D.S.
Angewandte Chemie - International Edition , 1999
147.
Generation of diazo-2-methylenecyclopropane and its 1,3-dipolar cycloaddition to acrylates
Tomilov Y.V., Klimenko I.P., Shulishov E.V., Nefedov O.M.
Russian Chemical Bulletin , 2000
148.
(1R,2R)-(-)-Bis(methoxycarbonyl)- spiropentane
Baldwin J.E., Sakkab D.H.
Journal of Organic Chemistry , 1995
149.
symm-Tetramethylenecyclooctane: En Route to Polyspirocycles
Averina E.B., Sedenkova K.N., Bakhtin S.G., Grishin Y.K., Kutateladze A.G., Roznyatovsky V.A., Rybakov V.B., Butov G.M., Kuznetsova T.S., Zefirov N.S.
Journal of Organic Chemistry , 2014
150.
Efficient Synthesis of 4-Methylene-L-glutamic Acid and its Analogues
Ouerfelli O., Ishida M., Shinozaki H., Nakanishi K., Ohfune Y.
Synlett , 1993
151.
Structural Requirements of 2-Oxoglutaric Acid Analogues To Mimic Its Signaling Function
Liu X., Wang Y., Laurini E., Posocco P., Chen H., Ziarelli F., Janicki A., Qu F., Fermeglia M., Pricl S., Zhang C., Peng L.
Organic Letters , 2013
152.
Discovery of a Biaryl Cyclohexene Carboxylic Acid (MK-6892): A Potent and Selective High Affinity Niacin Receptor Full Agonist with Reduced Flushing Profiles in Animals as a Preclinical Candidate
Shen H.C., Ding F., Raghavan S., Deng Q., Luell S., Forrest M.J., Carballo-Jane E., Wilsie L.C., Krsmanovic M.L., Taggart A.K., Wu K.K., Wu T., Cheng K., Ren N., Cai T., et. al.
Journal of Medicinal Chemistry , 2010
153.
Efficient synthesis of 4-methylene-L-glutamic acid and its cyclopropyl analogue
Eacquerra J., Pedregal C., Micó I., Nájera C.
Tetrahedron Asymmetry , 1994
154.
Asymmetric Synthesis of Conformationally Constrained trans-2,3-Piperidinedicarboxylic Acid Derivatives
Yao W., Zhuo J., Burns D., Zhang C., Xu M., Weng L., Qian D., He C., Lin Q., Li Y., Shi E., Agrios C., Metcalf B.
Synlett , 2007
155.
Discovery of potent, selective 4-fluoroproline-based thrombin inhibitors with improved metabolic stability
Staas D.D., Savage K.L., Sherman V.L., Shimp H.L., Lyle T.A., Tran L.O., Wiscount C.M., McMasters D.R., Sanderson P.E., Williams P.D., Lucas B.J., Krueger J.A., Dale Lewis S., White R.B., Yu S., et. al.
Bioorganic and Medicinal Chemistry , 2006
156.
rcr_90_2_199bib156
Moody
1997
158.
Aromatic Spiroketal Bisphosphine Ligands: Palladium-Catalyzed Asymmetric Allylic Amination of Racemic Morita-Baylis-Hillman Adducts
Wang X., Meng F., Wang Y., Han Z., Chen Y., Liu L., Wang Z., Ding K.
Angewandte Chemie - International Edition , 2012
159.
Structural development of p-carborane-based potent non-secosteroidal vitamin D analogs
Fujii S., Sekine R., Kano A., Masuno H., Songkram C., Kawachi E., Hirano T., Tanatani A., Kagechika H.
Bioorganic and Medicinal Chemistry , 2014
160.
Enantiomerically Pure Cyclopropylamines from Cyclopropylboronic Esters
Pietruszka J., Solduga G.
European Journal of Organic Chemistry , 2009
161.
rcr_90_2_199bib161
Pietruszka
2000
162.
Catalytic Cyclopropanation of Ricinolic Acid Derivatives with Diazomethane
Davletbakova A.M., Maidanova I.O., Baibulatova N.Z., Dokichev V.A., Tomilov Y.V., Yunusov M.S., Nefedov O.M.
Russian Journal of Organic Chemistry , 2001
164.
Comparative Analysis of Small Molecules and Histone Substrate Analogues as LSD1 Lysine Demethylase Inhibitors
Culhane J.C., Wang D., Yen P.M., Cole P.A.
Journal of the American Chemical Society , 2010
167.
Novel Erythromycin Derivatives with Aryl Groups Tethered to the C-6 Position Are Potent Protein Synthesis Inhibitors and Active against Multidrug-Resistant Respiratory Pathogens
Ma Z., Clark R.F., Brazzale A., Wang S., Rupp M.J., Li L., Griesgraber G., Zhang S., Yong H., Phan L.T., Nemoto P.A., Chu D.T., Plattner J.J., Zhang X., Zhong P., et. al.
Journal of Medicinal Chemistry , 2001
168.
Arylcyclopropanecarboxyl Guanidines as Novel, Potent, and Selective Inhibitors of the Sodium Hydrogen Exchanger Isoform-1
Ahmad S., Doweyko L.M., Dugar S., Grazier N., Ngu K., Wu S.C., Yost K.J., Chen B., Gougoutas J.Z., DiMarco J.D., Lan S., Gavin B.J., Chen A.Y., Dorso C.R., Serafino R., et. al.
Journal of Medicinal Chemistry , 2001
169.
Structure–activity relationship of triaryl propionic acid analogues on the human EP 3 prostanoid receptor
Gallant M., Belley M., Carrière M., Chateauneuf A., Denis D., Lachance N., Lamontagne S., Metters K.M., Sawyer N., Slipetz D., Truchon J.F., Labelle M.
Bioorganic and Medicinal Chemistry Letters , 2003
170.
Design, synthesis, and biological evaluation of 8-biarylquinolines: A novel class of PDE4 inhibitors
Gallant M., Chauret N., Claveau D., Day S., Deschênes D., Dubé D., Huang Z., Lacombe P., Laliberté F., Lévesque J., Liu S., Macdonald D., Mancini J., Masson P., Mastracchio A., et. al.
Bioorganic and Medicinal Chemistry Letters , 2008
172.
SYNTHESIS OF METHYL trans-2-PHENYLCYCLOPROPANE CARBOXYLATES
Beres J.A., Crouch R.D.
Organic Preparations and Procedures International , 1988
173.
trans-2-Aryl-N,N-dipropylcyclopropylamines:  Synthesis and Interactions with 5-HT1A Receptors
Vallgårda J., Appelberg U., Arvidsson L., Hjorth S., Svensson B.E., Hacksell U.
Journal of Medicinal Chemistry , 1996
174.
Facile synthesis of substituted trans-2-arylcyclopropylamine inhibitors of the human histone demethylase LSD1 and monoamine oxidases A and B
Gooden D.M., Schmidt D.M., Pollock J.A., Kabadi A.M., McCafferty D.G.
Bioorganic and Medicinal Chemistry Letters , 2008
176.
Novel trans-2-aryl-cyclopropylamine analogues as potent and selective dipeptidyl peptidase IV inhibitors
Tsai T., Hsu T., Chen C., Cheng J., Yeh T., Chen X., Huang C., Chang C., Yeh K., Hsieh S., Chien C., Chang Y., Huang C., Huang Y., Huang C., et. al.
Bioorganic and Medicinal Chemistry , 2009
177.
Asymmetric cyclopropanation using amino acid as chiral auxiliary
Mitra D., Sengupta A., Biradha K., Basak A.
Tetrahedron Asymmetry , 2008
178.
Design and synthesis of benzoxazole derivatives as novel melatoninergic ligands
Sun L., Chen J., Takaki K., Johnson G., Iben L., Mahle C.D., Ryan E., Xu C.
Bioorganic and Medicinal Chemistry Letters , 2004
179.
N-{2-[2-(4-Phenylbutyl)benzofuran-4-yl]cyclopropylmethyl}acetamide: an orally bioavailable melatonin receptor agonist
Sun L., Takaki K., Chen J., Iben L., Knipe J.O., Pajor L., Mahle C.D., Ryan E., Xu C.
Bioorganic and Medicinal Chemistry Letters , 2004
181.
SAR studies of 3-arylpropionic acids as potent and selective agonists of sphingosine-1-phosphate receptor-1 (S1P1) with enhanced pharmacokinetic properties
Yan L., Huo P., Hale J.J., Mills S.G., Hajdu R., Keohane C.A., Rosenbach M.J., Milligan J.A., Shei G., Chrebet G., Bergstrom J., Card D., Mandala S.M.
Bioorganic and Medicinal Chemistry Letters , 2007
182.
3′,4′-Bis-difluoromethoxycinnamoylanthranilate (FT061): An orally-active antifibrotic agent that reduces albuminuria in a rat model of progressive diabetic nephropathy
Williams S.J., Zammit S.C., Cox A.J., Shackleford D.M., Morizzi J., Zhang Y., Powell A.K., Gilbert R.E., Krum H., Kelly D.J.
Bioorganic and Medicinal Chemistry Letters , 2013
183.
trans-2-(2,5-Dimethoxy-4-iodophenyl)cyclopropylamine and trans-2-(2,5-dimethoxy-4-bromophenyl)cyclopropylamine as potent agonists for the 5-HT2 receptor family
Pigott A., Frescas S., McCorvy J.D., Huang X., Roth B.L., Nichols D.E.
Beilstein Journal of Organic Chemistry , 2012
184.
rcr_90_2_199bib184
Davi
2008
185.
Cyclopropanation with Diazomethane and Bis(oxazoline)palladium(II) Complexes
Denmark S.E., Stavenger R.A., Faucher A., Edwards J.P.
Journal of Organic Chemistry , 1997
186.
Synthesis and evaluation of (E)-2-(acrylamido)cyclohex-1-enecarboxylic acid derivatives as HCA1, HCA2, and HCA3 receptor agonists
Bobileva O., Bokaldere R., Gailite V., Kaula I., Ikaunieks M., Duburs G., Petrovska R., Mandrika I., Klovins J., Loza E.
Bioorganic and Medicinal Chemistry , 2014
187.
Characterization of the Binding Site of the Histamine H3 Receptor. 1. Various Approaches to the Synthesis of 2-(1H-Imidazol-4-yl)cyclopropylamine and Histaminergic Activity of (1R,2R)- and (1S,2S)-2-(1H-Imidazol-4-yl)- cyclopropylamine
De Esch I.J., Vollinga R.C., Goubitz K., Schenk H., Appelberg U., Hacksell U., Lemstra S., Zuiderveld O.P., Hoffmann M., Leurs R., Menge W.M., Timmerman H.
Journal of Medicinal Chemistry , 1999
188.
Synthesis and Serotonin Receptor Affinities of a Series of trans-2-(Indol-3-yl)cyclopropylamine Derivatives
Vangveravong S., Kanthasamy A., Lucaites V.L., Nelson D.L., Nichols D.E.
Journal of Medicinal Chemistry , 1998
189.
Conformationally restricted homotryptamines. Part 4: Heterocyclic and naphthyl analogs of a potent selective serotonin reuptake inhibitor
Dalton King H., Denhart D.J., Deskus J.A., Ditta J.L., Epperson J.R., Higgins M.A., Kung J.E., Marcin L.R., Sloan C.P., Mattson G.K., Molski T.F., Krause R.G., Bertekap R.L., Lodge N.J., Mattson R.J., et. al.
Bioorganic and Medicinal Chemistry Letters , 2007
190.
Conformationally Restricted Homotryptamines. 2. Indole Cyclopropylmethylamines as Selective Serotonin Reuptake Inhibitors
Mattson R.J., Catt J.D., Denhart D.J., Deskus J.A., Ditta J.L., Higgins M.A., Marcin L.R., Sloan C.P., Beno B.R., Gao Q., Cunningham M.A., Mattson G.K., Molski T.F., Taber M.T., Lodge N.J., et. al.
Journal of Medicinal Chemistry , 2005
193.
Synthesis of Enantiomerically Pure Cyclopropanes from Cyclopropylboronic Acids
Luithle J.E., Pietruszka J.
Journal of Organic Chemistry , 1999
194.
Kinetic Enzymatic Resolution of Cyclopropane Derivatives
Pietruszka J., Rieche A. ., Wilhelm T., Witt A.
Advanced Synthesis and Catalysis , 2003
195.
rcr_90_2_199bib195
Luithle
1998
196.
Synthesis of “Garner” Aldehyde-Derived Cyclopropylboronic Esters
Pietruszka J., Witt A., Frey W.
European Journal of Organic Chemistry , 2003
200.
Synthesis and biological evaluation of enantiomerically pure cyclopropyl analogues of combretastatin A4
Ty N., Pontikis R., Chabot G.G., Devillers E., Quentin L., Bourg S., Florent J.
Bioorganic and Medicinal Chemistry , 2013
201.
rcr_90_2_199bib201
Pietruszka
Synlett , 2003
204.
Synthesis and antitumor-evaluation of cyclopropyl-containing combretastatin analogs
Fürst R., Zupkó I., Berényi Á., Ecker G.F., Rinner U.
Bioorganic and Medicinal Chemistry Letters , 2009
205.
Synthesis and Biological Characterization of Aryl Uracil Inhibitors of Hepatitis C Virus NS5B Polymerase: Discovery of ABT-072, a trans-Stilbene Analog with Good Oral Bioavailability
Randolph J.T., Krueger A.C., Donner P.L., Pratt J.K., Liu D., Motter C.E., Rockway T.W., Tufano M.D., Wagner R., Lim H.B., Beyer J.M., Mondal R., Panchal N.S., Colletti L., Liu Y., et. al.
Journal of Medicinal Chemistry , 2018
206.
Naphthamidine urokinase plasminogen activator inhibitors with improved pharmacokinetic properties
Bruncko M., McClellan W.J., Wendt M.D., Sauer D.R., Geyer A., Dalton C.R., Kaminski M.A., Weitzberg M., Gong J., Dellaria J.F., Mantei R., Zhao X., Nienaber V.L., Stewart K., Klinghofer V., et. al.
Bioorganic and Medicinal Chemistry Letters , 2005
207.
Preparation of novel anthranilic acids as antibacterial agents. Extensive evaluation of alternative amide bioisosteres connecting the A- and the B-rings
Thorarensen A., Wakefield B.D., Romero D.L., Marotti K.R., Sweeney M.T., Zurenko G.E., Rohrer D.C., Han F., Bryant G.L.
Bioorganic and Medicinal Chemistry Letters , 2007
208.
Discovery of a novel series of potent non-nucleoside inhibitors of hepatitis C virus NS5B.
Schoenfeld R.C., Bourdet D.L., Brameld K.A., Chin E., de Vicente J., Fung A., Harris S.F., Lee E.K., Le Pogam S., Leveque V., Li J., Lui A.S., Najera I., Rajyaguru S., Sangi M., et. al.
Journal of Medicinal Chemistry , 2013
209.
Structure−Activity Relationship Studies on 1-[2-(4-Phenylphenoxy)ethyl]pyrrolidine (SC-22716), a Potent Inhibitor of Leukotriene A4 (LTA4) Hydrolase
Penning T.D., Chandrakumar N.S., Chen B.B., Chen H.Y., Desai B.N., Djuric S.W., Docter S.H., Gasiecki A.F., Haack R.A., Miyashiro J.M., Russell M.A., Yu S.S., Corley D.G., Durley R.C., Kilpatrick B.F., et. al.
Journal of Medicinal Chemistry , 2000
210.
Novel substituted isoxazole FXR agonists with cyclopropyl, hydroxycyclobutyl and hydroxyazetidinyl linkers: Understanding and improving key determinants of pharmacological properties
Kinzel O., Steeneck C., Schlüter T., Schulz A., Gege C., Hahn U., Hambruch E., Hornberger M., Spalwisz A., Frick K., Perović-Ottstadt S., Deuschle U., Burnet M., Kremoser C.
Bioorganic and Medicinal Chemistry Letters , 2016
211.
Total Synthesis of Solandelactones A and B
Eichenauer N.C., Nordschild A.C., Bischop M., Schumacher D., Mackwitz M.K., Tschersich R., Wilhelm T., Pietruszka J.
European Journal of Organic Chemistry , 2015
212.
Adducts of Bromo- and Dibromocarbenes with Dicyclo[6.1.0]non-2-ene and Tricyclo[8.1.0.01,9.04,6]deca-2,6-diene in Reaction with Potassium tert-Butylate
Averina E.B., Budynina E.M., Grishin Y.K., Zefirov A.N., Kuznetsova T.S., Zefirov N.S.
Russian Journal of Organic Chemistry , 2001
215.
Stereoselective synthesis of chiral polyfunctionalized cyclohexane derivatives. Palladium(II)-mediated reaction between cyclohexenones and diazomethane
Rodrı́guez-Garcı́a C., Ibarzo J., Álvarez-Larena Á., Branchadell V., Oliva A., Ortuño R.M.
Tetrahedron , 2001
218.
Discovery and Development of 3-(6-Chloropyridine-3-yloxymethyl)-2-azabicyclo[3.1.0]hexane Hydrochloride (SUVN-911): A Novel, Potent, Selective, and Orally Active Neuronal Nicotinic Acetylcholine α4β2 Receptor Antagonist for the Treatment of Depression
Nirogi R., Mohammed A.R., Shinde A.K., Ravella S.R., Bogaraju N., Subramanian R., Mekala V.R., Palacharla R.C., Muddana N., Thentu J.B., Bhyrapuneni G., Abraham R., Jasti V.
Journal of Medicinal Chemistry , 2020
219.
Synthesis of Functionalized Pyrrolidin-2-ones and (S)-Vigabatrin from Pyrrole
Gheorghe A., Schulte M., Reiser O.
Journal of Organic Chemistry , 2006
220.
Estrogen receptor ligands. Part 7: Dihydrobenzoxathiin SERAMs with bicyclic amine side chains
Blizzard T.A., DiNinno F., Morgan J.D., Chen H.Y., Wu J.Y., Gude C., Kim S., Chan W., Birzin E.T., Tien Yang Y., Pai L., Zhang Z., Hayes E.C., DaSilva C.A., Tang W., et. al.
Bioorganic and Medicinal Chemistry Letters , 2004
221.
Development of 2′-Substituted (2S,1′R,2′S)-2-(Carboxycyclopropyl)glycine Analogues as Potent N-Methyl-d-aspartic Acid Receptor Agonists
Risgaard R., Nielsen S.D., Hansen K.B., Jensen C.M., Nielsen B., Traynelis S.F., Clausen R.P.
Journal of Medicinal Chemistry , 2013
222.
Synthesis of cyclic α-hydrazino acids
Duttagupta I., Goswami K., Sinha S.
Tetrahedron , 2012
224.
Reactions of levoglucosenone and its derivatives with diazo compounds
Novikov R.A., Rafikov R.R., Shulishov E.V., Konyushkin L.D., Semenov V.V., Tomilov Y.V.
Russian Chemical Bulletin , 2009
225.
Polycyclic N-Benzamido Imides with Potent Activity against Vaccinia Virus
Torres E., Duque M.D., Camps P., Naesens L., Calvet T., Font-Bardia M., Vázquez S.
ChemMedChem , 2010
226.
Exploring the Size Limit of Templates for Inhibitors of the M2 Ion Channel of Influenza A Virus
Duque M.D., Ma C., Torres E., Wang J., Naesens L., Juárez-Jiménez J., Camps P., Luque F.J., DeGrado W.F., Lamb R.A., Pinto L.H., Vázquez S.
Journal of Medicinal Chemistry , 2011
228.
The first synthesis of a 2′,3′-methano carbocyclic nucleoside
Katagiri N., Yamatoya Y., Ishikura M.
Tetrahedron Letters , 1999
229.
Synthesis of carbocyclic nucleosides bearing a cyclopropane ring
Yamatoya Y., Ishikura M., Katagiri N.
Nucleic Acids Symposium Series , 1999
232.
Novel inhibitors of hepatitis C NS3–NS4A serine protease derived from 2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid
Venkatraman S., Njoroge F.G., Wu W., Girijavallabhan V., Prongay A.J., Butkiewicz N., Pichardo J.
Bioorganic and Medicinal Chemistry Letters , 2006
233.
Synthesis of Cyclopropanated 7-Oxabenzonorbornadienes
Tam W., McKee M., Haner J., Carlson E.
Synthesis , 2014
235.
Synthesis of cyclopropanated [2.2.1] heterobicycloalkenes: An improved procedure
Carlson E., Duret G., Blanchard N., Tam W.
Synthetic Communications , 2015
237.
Palladium Catalyzed Cyclopropanation of Unsaturated Endoperoxides. A New Peroxide Preserving Reaction.
Emerzian M., Davenport W., Song J., Li J., Erden I.
Advanced Synthesis and Catalysis , 2009
239.
Discovery of a nortropanol derivative as a potent and orally active GPR119 agonist for type 2 diabetes
Xia Y., Chackalamannil S., Greenlee W.J., Jayne C., Neustadt B., Stamford A., Vaccaro H., Xu X.(., Baker H., O’Neill K., Woods M., Hawes B., Kowalski T.
Bioorganic and Medicinal Chemistry Letters , 2011
240.
Model studies toward the synthesis of the bioactive diterpenoid, harringtonolide
O'Sullivan T.P., Zhang H., Mander L.N.
Organic and Biomolecular Chemistry , 2007
241.
rcr_90_2_199bib241
Vallgårda
1994
242.
(R)-2-(4-Phenylbutyl)dihydrobenzofuran derivatives as melatoninergic agents
Sun L., Takaki K., Chen J., Bertenshaw S., Iben L., Mahle C.D., Ryan E., Wu D., Gao Q., Xu C.
Bioorganic and Medicinal Chemistry Letters , 2005
243.
From ATP to AZD6140: The discovery of an orally active reversible P2Y12 receptor antagonist for the prevention of thrombosis
Springthorpe B., Bailey A., Barton P., Birkinshaw T.N., Bonnert R.V., Brown R.C., Chapman D., Dixon J., Guile S.D., Humphries R.G., Hunt S.F., Ince F., Ingall A.H., Kirk I.P., Leeson P.D., et. al.
Bioorganic and Medicinal Chemistry Letters , 2007
244.
Tranylcypromine Substituted cis-Hydroxycyclobutylnaphthamides as Potent and Selective Dopamine D3 Receptor Antagonists
Chen J., Levant B., Jiang C., Keck T.M., Newman A.H., Wang S.
Journal of Medicinal Chemistry , 2014
245.
rcr_90_2_199bib245
Tuhina
2002
247.
Design and synthesis of dipeptidyl nitriles as potent, selective, and reversible inhibitors of cathepsin C
Guay D., Beaulieu C., Jagadeeswar Reddy T., Zamboni R., Methot N., Rubin J., Ethier D., David Percival M.
Bioorganic and Medicinal Chemistry Letters , 2009
248.
Discovery of novel spirocyclic inhibitors of fatty acid amide hydrolase (FAAH). Part 1: Identification of 7-azaspiro[3.5]nonane and 1-oxa-8-azaspiro[4.5]decane as lead scaffolds
Meyers M.J., Long S.A., Pelc M.J., Wang J.L., Bowen S.J., Walker M.C., Schweitzer B.A., Madsen H.M., Tenbrink R.E., McDonald J., Smith S.E., Foltin S., Beidler D., Thorarensen A.
Bioorganic and Medicinal Chemistry Letters , 2011
250.
Sequential Peripheral Cyclopropanation as a Synthetic Approach to Cyclosubstituted Triangulanes
Zefirov N.S., Kuznetsova T.S., Eremenko O.V., Kokoreva O.V., Zatonsky G., Ugrak B.I.
Journal of Organic Chemistry , 1994
251.
Synthesis of alicyclic derivatives of spiropentane based on 1,5-cyclooctadiene
Kuznetsova T.S., Eremenko O.V., Kokoreva O.V., Zatonsky G.V., Zefiov N.S.
Russian Chemical Bulletin , 1996
252.
rcr_90_2_199bib252
Lukin
Zh. Org. Khim. , 1988
253.
rcr_90_2_199bib253
Kuznetsova
Russ. J. Org. Chem. , 2000
254.
New oxirane derivatives of 1,4-naphthoquinones and their evaluation against T. cruzi epimastigote forms
Carneiro P.F., do Nascimento S.B., Pinto A.V., Pinto M.D., Lechuga G.C., Santos D.O., dos Santos Júnior H.M., Resende J.A., Bourguignon S.C., Ferreira V.F.
Bioorganic and Medicinal Chemistry , 2012
258.
Catalytic Cyclopropanation of Fluorine-Containing Alkenes and Dienes with Diazomethane and Methyl Diazoacetate
Guseva E., Volchkov N., Tomilov Y., Nefedov O.
European Journal of Organic Chemistry , 2004
260.
Catalytic asymmetric inverse electron demand Diels–Alder reaction of fulvenes with azoalkenes
Wei L., Zhu Q., Song Z., Liu K., Wang C.
Chemical Communications , 2018
261.
rcr_90_2_199bib261
Frey
Z. Kristallogr. – New Cryst. Struct. , 2011
263.
Highly Concise Routes to Epothilones:  The Total Synthesis and Evaluation of Epothilone 490
Biswas K., Lin H., Njardarson J.T., Chappell M.D., Chou T., Guan Y., Tong W.P., He L., Horwitz S.B., Danishefsky S.J.
Journal of the American Chemical Society , 2002
265.
Cyclopropanation of methyl (2E)-3-[(1R,6S)-7,7-dimethyl-2-oxo-3-oxabicyclo[4.1.0]hept-4-en-4-yl]prop-2-enoate with dichlorocarbene and diazomethane
Kasradze V.G., Kukovinets O.S., Salimova E.V., Gilyazetdinova I.I., Khanova M.D., Lobov A.N., Galin F.Z.
Russian Journal of Organic Chemistry , 2009
266.
Spiro[2.4]hepta-4,6-dienes: synthesis and chemical reactions
Menchikov L.G., Nefedov O.M.
Russian Chemical Reviews , 1994
267.
Spiro[2.4]hepta-4,6-dienes: synthesis and application in organic synthesis
Menchikov L.G., Nefedov O.M.
Russian Chemical Reviews , 2016
268.
Ambiguousness of GC-MS identification of spiro[2.4]hepta-4,6-diene in natural objects
Menchikov L.G., Nefedov O.M., Zenkevich I.G.
Russian Chemical Bulletin , 2017
269.
Structure–activity relationship studies on ortho-substituted cinnamic acids, a new class of selective EP3 antagonists
Belley M., Gallant M., Roy B., Houde K., Lachance N., Labelle M., Trimble L.A., Chauret N., Li C., Sawyer N., Tremblay N., Lamontagne S., Carrière M., Denis D., Greig G.M., et. al.
Bioorganic and Medicinal Chemistry Letters , 2005
270.
Cyclopropanation reactions catalysed by dendrimers possessing one metalloporphyrin active site at the core: linear and sigmoidal kinetic behaviour for different dendrimer generations
Vinš P., de Cózar A., Rivilla I., Nováková K., Zangi R., Cvačka J., Arrastia I., Arrieta A., Drašar P., Miranda J.I., Cossío F.P.
Tetrahedron , 2016
273.
rcr_90_2_199bib273
Nefedov
1990
274.
Syntheses and Properties of Enantiomerically Pure Higher (n ≥ 7) [n−2]Triangulanedimethanols and σ-[n]Helicenes
de Meijere A., Khlebnikov A.F., Kozhushkov S.I., Yufit D.S., Chetina O.V., Howard J.A., Kurahashi T., Miyazawa K., Frank D., Schreiner P.R., Rinderspacher B.C., Fujisawa M., Yamamoto C., Okamoto Y.
Chemistry - A European Journal , 2006
275.
Synthesis, Reactions, and Rearrangements of 2,4-Diazabicyclo[3.1.0]hexan-3-ones
Quast H., Walter Stawitz J., Mueller B.
Heterocycles , 2012
276.
Thebaine Cyclopropanation
Schultz E.E., Shakirov M.M., Bagryanskaya I.Y., Gatilov Y.V., Tolstikov G.A., Kalinin V.N., Schmidhammer H.
Russian Journal of Organic Chemistry , 2003
277.
Regio- and stereoselective method for the synthesis of 6?,7?-methylene-6,7-dihydrothebaine
Sultanov S.Z., Dokichev V.A., Shults E.E., Dzhemilev U.M., Tolstikov G.A., Nefedov O.M.
Russian Chemical Bulletin , 1994
278.
rcr_90_2_199bib278
Arnone
2001
279.
Preparation and Structure Determination of a Stable cis-Bis-σ-homobenzene Derivative
Wullbrandt D., Hopf H., Jones P.G.
European Journal of Organic Chemistry , 2010
280.
Platinum-catalysed cyclopropanation of olefins with ethyl diazoacetate
Boverie S., Simal F., Demonceau A., Noels A.F., Eremenko I.L., Sidorov A.A., Nefedov S.E.
Tetrahedron Letters , 1997
281.
Catalytic transformations of diazo compounds promoted by platinum(0) and dicationic platinum(II) complexes
Bertani R., Biasiolo M., Darini K., Michelin R.A., Mozzon M., Visentin F., Zanotto L.
Journal of Organometallic Chemistry , 2002