Abstract
Multicomponent reactions of diazo compounds catalyzed by Rh$^\mathrm{II}$ complexes become a~powerful tool for organic synthesis. They enable three- or four-step processes to be carried out as one-pot procedures (actually as one step) with high stereoselectivity to give complex organic molecules, including biologically active compounds. This review addresses recent results in the chemistry of Rh-catalyzed multicomponent reactions of diazocarbonyl compounds with the intermediate formation of N-, O- and C=O--ylides. The diastereo- and enantioselectivity of these reactions and the possibility of using various co-catalysts to increase the efficiency of the processes under consideration are discussed.
The bibliography includes 120 references.
References
1.
Huisgen R.
Angewandte Chemie ,
1955
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. ,
1956
3.
3
M. F. Shostakovskii
"Prostye Vinilovye Efiry" (Vinyl Ethers) ,
1952
4.
4
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1949
5.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1953
6.
7.
Maas G.
Topics in Current Chemistry ,
1987
8.
8
V. N. Kondrat'ev
"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) ,
1959
9.
Padwa A., Hornbuckle S.F.
Chemical Reviews ,
1991
10.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) ,
1959
11.
11
T. T. Bannister
Diss. Abstr. ,
1959
13.
Davies H.M., Beckwith R.E.
Chemical Reviews ,
2003
14.
Lebel H., Marcoux J., Molinaro C., Charette A.B.
Chemical Reviews ,
2003
15.
Davies H.M., Hedley S.J.
Chemical Society Reviews ,
2007
16.
Hansen J., Davies H.M.
Coordination Chemistry Reviews ,
2008
17.
Zhang Z., Wang J.
Tetrahedron ,
2008
18.
Davies H.M., Manning J.R.
Nature ,
2008
19.
Doyle M.P., Duffy R., Ratnikov M., Zhou L.
Chemical Reviews ,
2009
20.
Herrmann P., Bach T.
Chemical Society Reviews ,
2011
21.
Collet F., Lescot C., Dauban P.
Chemical Society Reviews ,
2011
22.
Davies H.M., Morton D.
Chemical Society Reviews ,
2011
23.
Rosenberg M.L., Krivokapic A., Tilset M.
Organic Letters ,
2008
24.
Rosenberg M.L., Vlašaná K., Gupta N.S., Wragg D., Tilset M.
Journal of Organic Chemistry ,
2011
25.
Rosenberg M.L., Langseth E., Krivokapic A., Gupta N.S., Tilset M.
New Journal of Chemistry ,
2011
26.
Rosenberg M.L., Krapp A., Tilset M.
Organometallics ,
2011
27.
Chan W., Lo S., Zhou Z., Yu W.
Journal of the American Chemical Society ,
2012
28.
Hyster T.K., Ruhl K.E., Rovis T.
Journal of the American Chemical Society ,
2013
29.
Shi Z., Koester D.C., Boultadakis-Arapinis M., Glorius F.
Journal of the American Chemical Society ,
2013
30.
Yu X., Yu S., Xiao J., Wan B., Li X.
Journal of Organic Chemistry ,
2013
31.
Shi J., Yan Y., Li Q., Xu H.E., Yi W.
Chemical Communications ,
2014
32.
DeAngelis A., Dmitrenko O., Fox J.M.
Journal of the American Chemical Society ,
2012
33.
Candeias N.R., Gois P.M., Afonso C.A.
Journal of Organic Chemistry ,
2006
34.
Chamni S., He Q., Dang Y., Bhat S., Liu J.O., Romo D.
ACS Chemical Biology ,
2011
35.
Lian Y., Davies H.M.
Organic Letters ,
2012
36.
Bonderoff S.A., Padwa A.
Organic Letters ,
2013
37.
Gillingham D., Fei N.
Chemical Society Reviews ,
2013
38.
Müller P., Allenbach Y., Chappellet S., Ghanem A.
Synthesis ,
2006
39.
Lindsay V.N., Charette A.B.
ACS Catalysis ,
2012
40.
Trindade A.F., Coelho J.A., Afonso C.A., Veiros L.F., Gois P.M.
ACS Catalysis ,
2012
41.
Wang Y., Chen Z., Mi A., Hu W.
Chemical Communications ,
2004
42.
Huang H., Wang Y., Chen Z., Hu W.
Advanced Synthesis and Catalysis ,
2005
43.
Zhu Y., Zhai C., Yang L., Hu W.
European Journal of Organic Chemistry ,
2011
44.
Wang Y., Zhu Y., Chen Z., Mi A., Hu W., Doyle M.P.
Organic Letters ,
2003
45.
Zhu Y., Zhai C., Yue Y., Yang L., Hu W.
Chemical Communications ,
2009
46.
Jiang J., Xu H., Xi J., Ren B., Lv F., Guo X., Jiang L., Zhang Z., Hu W.
Journal of the American Chemical Society ,
2011
47.
Jing C., Xing D., Qian Y., Shi T., Zhao Y., Hu W.
Angewandte Chemie - International Edition ,
2013
48.
Jiang J., Ma X., Liu S., Qian Y., Lv F., Qiu L., Wu X., Hu W.
Chemical Communications ,
2013
49.
Wang C., Liu S., Xing D., Wang X., Wu X., Hu W.
Tetrahedron ,
2013
50.
Qiu L., Wang D., Lv F., Guo X., Hu W., Yang L., Liu S.
Tetrahedron ,
2014
51.
Zhang X., Ji J., Zhu Y., Jing C., Li M., Hu W.
Organic and Biomolecular Chemistry ,
2012
52.
Zhou C., Wang J., Wei J., Xu Z., Guo Z., Low K., Che C.
Angewandte Chemie - International Edition ,
2012
53.
Ren L., Lian X., Gong L.
Chemistry - A European Journal ,
2013
54.
Dawande S.G., Kanchupalli V., Lad B.S., Rai J., Katukojvala S.
Organic Letters ,
2014
55.
Hansen S.R., Spangler J.E., Hansen J.H., Davies H.M.
Organic Letters ,
2012
56.
Jing C., Xing D., Hu W.
Chemical Communications ,
2014
57.
Viso A., Fernández de la Pradilla R., García A., Flores A.
Chemical Reviews ,
2005
58.
Guo Z., Shi T., Jiang J., Yang L., Hu W.
Organic and Biomolecular Chemistry ,
2009
59.
Guan X., Yang L., Hu W.
Angewandte Chemie - International Edition ,
2010
60.
Qian Y., Xu X., Jiang L., Prajapati D., Hu W.
Journal of Organic Chemistry ,
2010
61.
Qian Y., Jing C., Shi T., Ji J., Tang M., Zhou J., Zhai C., Hu W.
ChemCatChem ,
2011
62.
Wang C., Xing D., Wang D., Wu X., Hu W.
Journal of Organic Chemistry ,
2014
63.
Lu C., Liu H., Chen Z., Hu W., Mi A.
Organic Letters ,
2004
64.
Huang H., Guo X., Hu W.
Angewandte Chemie - International Edition ,
2007
65.
Guo X., Huang H., Yang L., Hu W.
Organic Letters ,
2007
66.
Zhang X., Huang H., Guo X., Guan X., Yang L., Hu W.
Angewandte Chemie - International Edition ,
2008
67.
Hu W., Xu X., Zhou J., Liu W., Huang H., Hu J., Yang L., Gong L.
Journal of the American Chemical Society ,
2008
68.
Alcaide B., Almendros P., Aragoncillo C., Callejo R., Ruiz M.P., Torres M.R.
Journal of Organic Chemistry ,
2009
69.
Guo Z., Cai M., Jiang J., Yang L., Hu W.
Organic Letters ,
2010
70.
Xu X., Qian Y., Yang L., Hu W.
Chemical Communications ,
2011
71.
Ji J., Zhang X., Zhu Y., Qian Y., Zhou J., Yang L., Hu W.
Journal of Organic Chemistry ,
2011
72.
Han X., Jiang L., Tang M., Hu W.
Organic and Biomolecular Chemistry ,
2011
73.
Alcaide B., Almendros P., Aragoncillo C., Callejo R., Ruiz M.P., Torres M.R.
European Journal of Organic Chemistry ,
2012
74.
Jiang J., Guan X., Liu S., Ren B., Ma X., Guo X., Lv F., Wu X., Hu W.
Angewandte Chemie - International Edition ,
2012
75.
Qiu L., Gao L., Tang J., Wang D., Guo X., Liu S., Yang L., Li J., Hu W.
Journal of Organic Chemistry ,
2014
76.
Xu X., Zhou J., Yang L., Hu W.
Chemical Communications ,
2008
77.
Muthusamy S., Krishnamurthi J.
Tetrahedron Letters ,
2007
78.
Qian Y., Jing C., Liu S., Hu W.
Chemical Communications ,
2013
79.
Qiu L., Guo X., Ma C., Qiu H., Liu S., Yang L., Hu W.
Chemical Communications ,
2014
80.
Skaggs A.J., Lin E.Y., Jamison T.F.
Organic Letters ,
2002
81.
Lu C., Chen Z., Liu H., Hu W., Mi A., Doyle M.P.
Journal of Organic Chemistry ,
2004
82.
Muthusamy S., Gunanathan C., Nethaji M.
Journal of Organic Chemistry ,
2004
83.
Muthusamy S., Ramkumar R., Mishra A.K.
Tetrahedron Letters ,
2011
84.
Torssell S., Kienle M., Somfai P.
Angewandte Chemie - International Edition ,
2005
85.
DeAngelis A., Panne P., Yap G.P., Fox J.M.
Journal of Organic Chemistry ,
2008
86.
DeAngelis A., Taylor M.T., Fox J.M.
Journal of the American Chemical Society ,
2009
87.
Hashimoto Y., Itoh K., Kakehi A., Shiro M., Suga H.
Journal of Organic Chemistry ,
2013
88.
Rajasekaran T., Karthik G., Sridhar B., Subba Reddy B.V.
Organic Letters ,
2013
89.
Xu X., Guo X., Han X., Yang L., Hu W.
Organic Chemistry Frontiers ,
2014
90.
90
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1951
91.
Pirrung M.C., Kaliappan K.P.
Organic Letters ,
2000
92.
Muthusamy S., Babu S.A., Gunanathan C., Ganguly B., Suresh E., Dastidar P.
Journal of Organic Chemistry ,
2002
93.
Gan Y., Harwood L.M., Richards S.C., Smith I.E., Vinader V.
Tetrahedron Asymmetry ,
2009
94.
Shimada N., Oohara T., Krishnamurthi J., Nambu H., Hashimoto S.
Organic Letters ,
2011
95.
Suga H., Hashimoto Y., Yasumura S., Takezawa R., Itoh K., Kakehi A.
Journal of Organic Chemistry ,
2013
96.
96
L. M. Vorob'eva
Biokhimiya ,
1958
97.
Krishnamurthi J., Nambu H., Takeda K., Anada M., Yamano A., Hashimoto S.
Organic and Biomolecular Chemistry ,
2013
98.
Suga H., Ebiura Y., Fukushima K., Kakehi A., Baba T.
Journal of Organic Chemistry ,
2005
99.
Nikolaev V.V., Krylov I.S., Schulze B., Rodina L.L.
Russian Journal of Organic Chemistry ,
2005
100.
100
V. V. Zolotarev
Chem. Abs. ,
1941
101.
García Ruano J.L., Fraile A., Martín M.R., Núñez A.
Journal of Organic Chemistry ,
2006
102.
Shimada N., Anada M., Nakamura S., Nambu H., Tsutsui H., Hashimoto S.
Organic Letters ,
2008
103.
Bolm C., Saladin S., Kasyan A.
Organic Letters ,
2002
104.
Hodgson D.M., Glen R., Redgrave A.J.
Tetrahedron Letters ,
2002
105.
Mehta G., Muthusamy S.
Tetrahedron ,
2002
106.
Hodgson D.M., Glen R., Grant G.H., Redgrave A.J.
Journal of Organic Chemistry ,
2002
107.
Molchanov A.P., Diev V.V., Kopf J., Kostikov R.R.
Russian Journal of Organic Chemistry ,
2004
108.
108
F. Fichter
Helv. Chim. Acta ,
1924
109.
Padwa A.
Journal of Organometallic Chemistry ,
2005
110.
Nikolaev V., Hennig L., Sieler J., Rodina L., Schulze B., Nikolaev V.
Organic and Biomolecular Chemistry ,
2005
111.
Muthusamy S., Gnanaprakasam B., Suresh E.
Organic Letters ,
2005
112.
Nikolaev V.V., Heimgartner H., Linden A., Krylov I.S., Nikolaev V.A.
European Journal of Organic Chemistry ,
2006
113.
Nikolaev V., Hennig L., Heimgartner H., Schulze B., Nikolaev V.
Tetrahedron Letters ,
2006
114.
Suga H., Ishimoto D., Higuchi S., Ohtsuka M., Arikawa T., Tsuchida T., Kakehi A., Baba T.
Organic Letters ,
2007
115.
Shi B., Merten S., Wong D.K., Chu J.C., Liu L.L., Lam S.K., Jäger A., Wong W., Chiu P., Metz P.
Advanced Synthesis and Catalysis ,
2009
116.
Domingo L.R., Sáez J.A.
Journal of Organic Chemistry ,
2010
117.
Muthusamy S., Karikalan T., Suresh E.
Tetrahedron Letters ,
2011
118.
Padwa A.
Tetrahedron ,
2011
119.
Terada M., Toda Y.
Angewandte Chemie - International Edition ,
2012
120.
Enßle M., Buck S., Werz R., Maas G.
Arkivoc ,
2012
121.
Muthusamy S., Karikalan T.
Tetrahedron ,
2012
122.
Muthusamy S., Sivaguru M.
Tetrahedron Letters ,
2013