Catalytic asymmetric Michael reactions of acetaldehyde

被引:206
作者
Garcia-Garcia, Patricia [1 ]
Ladepeche, Arnaud [1 ]
Halder, Rajkumar [1 ]
List, Benjamin [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
asymmetric catalysis; Michael addition; nitroolefins; organocatalysis; synthetic methods;
D O I
10.1002/anie.200800847
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Acetaldehyde, now a big contender: A silyl prolinol derivative was found to catalyze the first Michael addition of acetaldehyde with both aromatic and aliphatic nitroolefins in excellent enantioselectivities (see scheme, TMS = trimethylsilyl). The utility of the reaction is illustrated in the synthesis of three current pharmaceuticals and in the synthesis of an enantiopure 3-monosubstituted pyrrolidine. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4719 / 4721
页数:3
相关论文
共 28 条
[21]   Catalytic asymmetric intramolecular α-alkylation of aldehydes [J].
Vignola, N ;
List, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) :450-451
[22]   Direct, highly enantioselective pyrrolidine sulfonamide catalyzed Michael addition of aldehydes to nitrostyrenes [J].
Wang, W ;
Wang, J ;
Li, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) :1369-1371
[23]  
Wang W., 2005, ANGEW CHEM, V117, P1393
[24]   An efficient enantioselective method for asymmetiric Michael addition of nitroalkanes to α,β-unsaturated aldehydes [J].
Wang, Yongcan ;
Li, Pengfei ;
Liang, Xinmiao ;
Zhang, Tony Y. ;
Ye, Jinxing .
CHEMICAL COMMUNICATIONS, 2008, (10) :1232-1234
[25]  
Wiesner M., 2008, ANGEW CHEM, V120, P1897
[26]   Tripeptides as efficient asymmetric catalysts for 1,4-addition reactions of aldehydes to nitroolefins - A rational approach [J].
Wiesner, Markus ;
Revell, Jefferson D. ;
Wennemers, Helma .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1871-1874
[27]   Proline-catalysed Mannich reactions of acetaldehyde [J].
Yang, Jung Woon ;
Chandler, Carley ;
Stadler, Michael ;
Kampen, Daniela ;
List, Benjamin .
NATURE, 2008, 452 (7186) :453-455
[28]   Highly enantioselective organocatalytic conjugate addition of nitromethane to α,β-unsaturated aldehydes:: Three-step synthesis of optically active baclofen [J].
Zu, Liansuo ;
Xie, Hexin ;
Li, Hao ;
Wang, Han ;
Wang, Wei .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) :2660-2664