Home / Articles / Ativated cyclopropanes in the synthesis of five-membered carbocycles and heterocycles

Ativated cyclopropanes in the synthesis of five-membered carbocycles and heterocycles

Oleg Grigor'evich Kulinkovich 1
Oleg Grigor'evich Kulinkovich
1 Belarusian State University, Minsk
Published 30 November 1992
Communication , Volume 62, Issue 9, 839-850
30
Share
Cite this
GOST
 | 
Cite this
GOST
Kulinkovich O. G. Ativated cyclopropanes in the synthesis of five-membered carbocycles and heterocycles // Russian Chemical Reviews. 1993. Vol. 62. No. 9. pp. 839-850.
GOST all authors (up to 50)
Kulinkovich O. G. Ativated cyclopropanes in the synthesis of five-membered carbocycles and heterocycles // Russian Chemical Reviews. 1993. Vol. 62. No. 9. pp. 839-850.
RIS
 | 
Cite this
RIS
TY - JOUR
DO - 10.1070/RC1993v062n09ABEH000049
UR - https://rcr.colab.ws/publications/10.1070/RC1993v062n09ABEH000049
TI - Ativated cyclopropanes in the synthesis of five-membered carbocycles and heterocycles
T2 - Russian Chemical Reviews
AU - Kulinkovich, Oleg Grigor'evich
PY - 1993
DA - 1992/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 839-850
IS - 9
VL - 62
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
@article{1993_Kulinkovich,
author = {Oleg Grigor'evich Kulinkovich},
title = {Ativated cyclopropanes in the synthesis of five-membered carbocycles and heterocycles},
journal = {Russian Chemical Reviews},
year = {1993},
volume = {62},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1993v062n09ABEH000049},
number = {9},
pages = {839--850},
doi = {10.1070/RC1993v062n09ABEH000049}
}
MLA
Cite this
MLA
Kulinkovich, Oleg Grigor'evich. “Ativated cyclopropanes in the synthesis of five-membered carbocycles and heterocycles.” Russian Chemical Reviews, vol. 62, no. 9, Nov. 1993, pp. 839-850. https://rcr.colab.ws/publications/10.1070/RC1993v062n09ABEH000049.
Views / Visits / Downloads
29 / 29 / 5

Abstract

The conversion of functionalised cyclopropane compounds to derivatives of cyclopentane and five-membered heterocycles is described. Topics discussed include reaction conditions, the regio- and stereo-selectivity of the reactions depending on the type of substituents in the three-membered ring, and also the main procedures for obtaining appropriate cyclopropane substrates. The bibliography includes 174 references.

References

1.
Ueber die Einwirkung von Aethylenbromid auf Malonsäureäther
Perkin W.H.
Berichte der deutschen chemischen Gesellschaft , 1884
2.
crKey-10.1070/RC1993v062n09ABEH000049-BIB2
1990
3.
crKey-10.1070/RC1993v062n09ABEH000049-BIB3
4.
crKey-10.1070/RC1993v062n09ABEH000049-BIB4
1966
5.
crKey-10.1070/RC1993v062n09ABEH000049-BIB5
1974
6.
crKey-10.1070/RC1993v062n09ABEH000049-BIB6
1985
7.
crKey-10.1070/RC1993v062n09ABEH000049-BIB7
1971
8.
crKey-10.1070/RC1993v062n09ABEH000049-BIB8
1980
9.
crKey-10.1070/RC1993v062n09ABEH000049-BIB9
10.
crKey-10.1070/RC1993v062n09ABEH000049-BIB10
1986
11.
Electrophilic cyclopropanes in organic synthesis
Danishefsky S.
Accounts of Chemical Research , 1979
12.
Nucleophilic Substitution Reactions of Cyclopropane Derivatives
Aksenov V.S., Terent'eva G.A., Savinykh Y.V.
Russian Chemical Reviews , 1980
13.
Oxycyclopropanes in organochemical synthesis
Wenkert E.
Accounts of Chemical Research , 1980
14.
Cyclopropanone hemiacetals
Salaun J.
Chemical Reviews , 1983
17.
Use of cyclopropanes and their derivatives in organic synthesis
Wong H.N., Hon M.Y., Tse C.W., Yip Y.C., Tanko J., Hudlicky T.
Chemical Reviews , 1989
18.
crKey-10.1070/RC1993v062n09ABEH000049-BIB20
1986
20.
Bond length changes resulting from halogen substitution on three-membered rings
Deakyne C.A., Allen L.C., Craig N.C.
Journal of the American Chemical Society , 1977
21.
Influence of substituents having lone pairs on the structure of cyclopropanes
Durmaz S., Kollmar H.
Journal of the American Chemical Society , 1980
22.
Substituent effects on the geometries and energies of cyclopropanes and the corresponding 2-propyl derivatives
Clark T., Spitznagel G.W., Klose R., Schleyer P.V.
Journal of the American Chemical Society , 1984
24.
Substituent effects on strain energies
Dill J.D., Greenberg A., Liebman J.F.
Journal of the American Chemical Society , 1979
25.
Nucleophilic eliminative ring fission
Stirling C.J.
Chemical Reviews , 1978
27.
crKey-10.1070/RC1993v062n09ABEH000049-BIB29
1988
28.
crKey-10.1070/RC1993v062n09ABEH000049-BIB30
Org. React. , 1985
29.
Thermal Rearrangements of Vinylcyclopropanes
Mil'vitskaya E.M., Tarakanova A.V., Plate A.F.
Russian Chemical Reviews , 1976
30.
Thermal unimolecular reactions of hydrocarbons
Frey H.M., Walsh R.
Chemical Reviews , 1969
31.
Mechanism of the vinylcyclopropane-cyclopentene rearrangement. Evidence against a concerted process
Mazzocchi P.H., Tamburin H.J.
Journal of the American Chemical Society , 1970
32.
crKey-10.1070/RC1993v062n09ABEH000049-BIB35
J. Mol. Struct.
33.
The vinylcyclopropane rearrangement: An AM1 study
Quirante J.J., Enriquez F., Hernando J.M.
Journal of Molecular Structure THEOCHEM , 1990
36.
crKey-10.1070/RC1993v062n09ABEH000049-BIB39
1986
37.
crKey-10.1070/RC1993v062n09ABEH000049-BIB40
Synthesis , 1984
38.
Anionic approaches to the construction of cyclopentanoids
Hudlicky T., Price J.D.
Chemical Reviews , 1989
39.
crKey-10.1070/RC1993v062n09ABEH000049-BIB42
Nouv. J. Chim. , 1981
43.
crKey-10.1070/RC1993v062n09ABEH000049-BIB46
1988
44.
(±)-Dicranenone A from 1-hydroxycyclopropanecarbaldehyde derivatives
Ollivier J., Salaün J.
Journal of the Chemical Society Chemical Communications , 1985
45.
crKey-10.1070/RC1993v062n09ABEH000049-BIB48
J. Am. Chem. Soc. , 1979
48.
crKey-10.1070/RC1993v062n09ABEH000049-BIB51
1987
50.
Dihydropyridine series. I. Novel and stable complexes of 1-methyl-3-ethyl-1,2-dihydropyridine and 1-methyl-3-ethyl-1,6-dihydropyridine
Bear C.A., Cullen W.R., Kutneny J.P., Ridaurua V.E., Trotter J., Zanarotti A.
Journal of the American Chemical Society , 1973
51.
Stereoselectivity and regiospecificity of spiroannelations with 1-lithiocyclopropyl phenyl sulfide
53.
New synthetic methods. A stereocontrolled approach to cyclopentane annelation
Trost B.M., Keeley D.E.
Journal of the American Chemical Society , 1976
57.
Cyclopropanation of unactivated 1,3-dienes by Fischer carbene complexes
Harvey D.F., Lund K.P.
Journal of the American Chemical Society , 1991
58.
Stereoselective synthesis of cyclopentene derivatives from 1,3-dienes
Danheiser R.L., Martinez-Davila C., Auchus R.J., Kadonaga J.T.
Journal of the American Chemical Society , 1981
63.
Reaction of 1,3-dithienium fluoroborate with 1,3-dienes. Synthesis of .DELTA.3-cyclopenten-1-ones
64.
Stereocontrolled total synthesis of pentalenenes via [2 + 3] and [4 + 1] cyclopentene annulation methodologies
65.
Stereoselective cyclopropanations with vinylcarbenoids
Davies H.M., Clark T.J., Church L.A.
Tetrahedron Letters , 1989
71.
crKey-10.1070/RC1993v062n09ABEH000049-BIB75
J. Org. Chem. , 1982
74.
The [2 + 3] and [3 + 4] annulation of enones. Enantiocontrolled total synthesis of (-)-retigeranic acid
Hudlicky T., Fleming A., Radesca L.
Journal of the American Chemical Society , 1989
76.
A shorter route to () estrone
Narasimhan N.S., Sunder N.M.
Tetrahedron Letters , 1988
79.
Oxycyclopropanes in organochemical synthesis. Total syntheses of (.+-.)-.alpha.-cuparenone and (.+-.)-.beta.-vetivone
Wenkert E., Buckwalter B.L., Craveiro A.A., Sanchez E.L., Sathe S.S.
Journal of the American Chemical Society , 1978
80.
Oxocyclopentenol syntheses
Wenkert E., Greenberg R.S., Raju M.S.
Journal of Organic Chemistry , 1985
82.
Facile synthesis of 2-substituted cyclopentenones
Baldwin S.W., Blomquist H.R.
Tetrahedron Letters , 1982
83.
Incursion of reversibility in Friedel-Crafts acylations
Agranat I., Shih Y.S., Bentor Y.
Journal of the American Chemical Society , 1974
90.
crKey-10.1070/RC1993v062n09ABEH000049-BIB95
Liebigs Ann. Chem. , 1982
91.
Asymmetric Synthesis of Methyl Jasmonate
Quinkert G., Adam F., Dürner G.
Angewandte Chemie - International Edition , 1982
95.
A total synthesis of pentalenolactone E methyl ester via a [3 + 2] annulation strategy
Marino J.P., Silveira C., Comasseto J., Petragnani N.
Journal of Organic Chemistry , 1987
96.
crKey-10.1070/RC1993v062n09ABEH000049-BIB101
Chem. Lett. , 1990
97.
General methods of alkaloid synthesis
Stevens R.V.
Accounts of Chemical Research , 1977
99.
Thermal rearrangement of cyclopropylimines. IV. Total synthesis of dl-mesembrine
Stevens R.V., Wentland M.P.
Journal of the American Chemical Society , 1968
105.
Synthesis of some substituted pyrrolidines from cyclopropyl carbonyl compounds
Blake K.W., Gillies I., Denney R.C.
Journal of the Chemical Society Perkin Transactions 1 , 1981
106.
crKey-10.1070/RC1993v062n09ABEH000049-BIB111
Khim. Geterotsikl. Soedin. , 1991
107.
crKey-10.1070/RC1993v062n09ABEH000049-BIB112
Khim. Geterotsikl. Soedin. , 1992
108.
crKey-10.1070/RC1993v062n09ABEH000049-BIB113
Zh. Org. Khim. , 1991
109.
crKey-10.1070/RC1993v062n09ABEH000049-BIB114
1993
110.
crKey-10.1070/RC1993v062n09ABEH000049-BIB115
Zh. Org. Khim. , 1993
111.
Formation of a pyrrole by carbene - carbene rearrangement
114.
crKey-10.1070/RC1993v062n09ABEH000049-BIB119
Angew. Chem., Int. Ed. Engl. , 1981
115.
Alkoxycarbenium Ions
Rakhmankulov D.L., Akhmatdinov R.T., Kantor E.A.
Russian Chemical Reviews , 1984
117.
crKey-10.1070/RC1993v062n09ABEH000049-BIB123
J. Chem. Soc, Perkin Trans. 2 , 1973
118.
crKey-10.1070/RC1993v062n09ABEH000049-BIB124
Khim. Geterotsikl. Soedin. , 1981
119.
crKey-10.1070/RC1993v062n09ABEH000049-BIB125
Zh. Org. Khim. , 1983
121.
Protonated cyclopropane intermediates in the reactions of cyclopropanecarboxylic acids
Deno N.C., Billups W.E., LaVietes D., Scholl P.C., Schneider S.
Journal of the American Chemical Society , 1970
123.
crKey-10.1070/RC1993v062n09ABEH000049-BIB129
Zh. Org. Khim. , 1980
124.
crKey-10.1070/RC1993v062n09ABEH000049-BIB130
Indian J. Chem. , 1983
125.
crKey-10.1070/RC1993v062n09ABEH000049-BIB131
Zh. Org. Khim. , 1983
127.
Bis(trimethylsilyl) Sulfate Catalysis in γ-Lactonization of Cyclopropanecarboxylates Activated by Carbonyl Substituents on α-Carbon
128.
Conversion of olefins into γ-butyrolactones
Brown S.P., Bal B.S., Pinnick H.W.
Tetrahedron Letters , 1981
129.
Synthesis of .alpha.-methylene-.gamma.-butyrolactones by rearrangements of cyclopropylcarbinyl substrates
Hudrlik P.F., Takacs J.M., Chou D.T., Rudnick L.R.
Journal of Organic Chemistry , 1979
131.
A novel synthesis of α-methylene-γ-butyrolactones from 1-(N,N-dimethylaminomethyl)cyclopropanecarboxylate esters
Hiyama T., Saimoto H., Nishio K., Shinoda M., Yamamoto H., Nozaki H.
Tetrahedron Letters , 1979
132.
Short syntheses of furan and catechol derivatives. A synthesis of hydrourushiol
Wenkert E., Alonso M.E., Buckwalter B.L., Sanchez E.L.
Journal of the American Chemical Society , 1983
133.
Synthese et reactivite d'oxycyclopropanes electrophiles
Abdallah H., Grée R., Carrié R.
Tetrahedron , 1985
134.
A method of synthesis of .beta.-methylfurans and .alpha.-methylene and .beta.-methylene .gamma.-lactones. Two menthofuran syntheses
Wenkert E., Alonso M.E., Buckwalter B.L., Chou K.J.
Journal of the American Chemical Society , 1977
135.
Total syntheses of eburnamonine, quebrachamine, vincadine and epivincadine
Wenkert E., Halls T.D., Kwart L.D., Magnusson G., Showalter H.D.
Tetrahedron , 1981
137.
Carbalkoxycarbenes
Marchand A.P., Brockway N.M.
Chemical Reviews , 1974
138.
crKey-10.1070/RC1993v062n09ABEH000049-BIB144
Liebigs Ann. Chem. , 1984
140.
crKey-10.1070/RC1993v062n09ABEH000049-BIB146
J. Chem. Res. (S) , 1985
142.
crKey-10.1070/RC1993v062n09ABEH000049-BIB148
Zh. Org. Khim. , 1986
143.
Capto-dative substituent effect on the cis-trans isomerisation of cyclopropanes
De Mesmaeker A., Vertommen L., Merényl R., Viehe H.G.
Tetrahedron Letters , 1982
145.
crKey-10.1070/RC1993v062n09ABEH000049-BIB151
Khim. Geterotsikl. Soedin. , 1984
146.
crKey-10.1070/RC1993v062n09ABEH000049-BIB152
Zh. Org. Khim. , 1984
147.
crKey-10.1070/RC1993v062n09ABEH000049-BIB153
Zh. Org. Khim. , 1982
148.
crKey-10.1070/RC1993v062n09ABEH000049-BIB154
Synthesis , 1984
149.
crKey-10.1070/RC1993v062n09ABEH000049-BIB155
Khim. Geterotsikl. Soedin. , 1988
150.
crKey-10.1070/RC1993v062n09ABEH000049-BIB156
Zh. Org. Khim. , 1975
151.
crKey-10.1070/RC1993v062n09ABEH000049-BIB157
Zh. Org. Khim. , 1975
152.
crKey-10.1070/RC1993v062n09ABEH000049-BIB158
Khim. Geterotsikl. Soedin. , 1984
153.
crKey-10.1070/RC1993v062n09ABEH000049-BIB159
Khim. Geterotsikl. Soedin. , 1983
154.
Kinetically controlled total syntheses of dl-trachelanthamidine and dl-isoretronecanol
Danishefsky S., McKee R., Singh R.K.
Journal of the American Chemical Society , 1977
156.
crKey-10.1070/RC1993v062n09ABEH000049-BIB162
J. Chem.Soc.,Chem.Commun. , 1985
157.
Thiophene Derivatives by Novel Rearrangements of Siloxy-substituted Cyclopropanecarboxylates
Brückner C., Reissig H.
Angewandte Chemie - International Edition , 1985
158.
crKey-10.1070/RC1993v062n09ABEH000049-BIB164
Liebigs Ann. Chem. , 1988
159.
crKey-10.1070/RC1993v062n09ABEH000049-BIB165
Liebigs Ann. Chem. , 1988
160.
A diastereoselective route to (±)-isoretronecanol
Flitsch W., Wernsmann P.
Tetrahedron Letters , 1981
161.
crKey-10.1070/RC1993v062n09ABEH000049-BIB167
Liebigs Ann. Chem. , 1983
162.
crKey-10.1070/RC1993v062n09ABEH000049-BIB168
Liebigs Ann. Chem. , 1983
164.
crKey-10.1070/RC1993v062n09ABEH000049-BIB170
Tetrahedron Lett. , 1975
165.
crKey-10.1070/RC1993v062n09ABEH000049-BIB171
1990
167.
crKey-10.1070/RC1993v062n09ABEH000049-BIB173
J. Am. Chem. Soc. , 1983
168.
Trichlorotitanium and alkoxytitanium homoenolates. Preparation, characterization, and utilization for organic synthesis
170.
crKey-10.1070/RC1993v062n09ABEH000049-BIB176
Liebigs Ann. Chem. , 1924
172.
crKey-10.1070/RC1993v062n09ABEH000049-BIB178
Chem. Lett. , 1989
173.
crKey-10.1070/RC1993v062n09ABEH000049-BIB179
Chem. Lett. , 1990
174.
crKey-10.1070/RC1993v062n09ABEH000049-BIB180
Chem. Lett. , 1990
175.
Optically active cyclopropanes
Salaun J.
Chemical Reviews , 1989