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
[1]   Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].
Betancort, JM ;
Barbas, CF .
ORGANIC LETTERS, 2001, 3 (23) :3737-3740
[2]   Direct catalytic asymmetric aldol reactions of aldehydes [J].
Bogevig, A ;
Kumaragurubaran, N ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2002, (06) :620-621
[3]   Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde [J].
Córdova, A ;
Notz, W ;
Barbas, CF .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :301-303
[4]   Diphenylprolinol silyl ether as catalyst of an asymmetric, catalytic, and direct Michael reaction of nitroalkanes with α,β-unsaturated aldehydes [J].
Gotoh, Hiroaki ;
Ishikawa, Hayato ;
Hayashi, Yujilro .
ORGANIC LETTERS, 2007, 9 (25) :5307-5309
[5]   Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes [J].
Hayashi, Y ;
Gotoh, H ;
Hayashi, T ;
Shoji, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (27) :4212-4215
[6]  
Hayashi Y., 2008, ANGEW CHEM, V120, P2112
[7]  
Hayashi Y., 2005, ANGEW CHEM, V117, P4284
[8]   A diarylprolinol in an asymmetric, catalytic, and direct crossed-aldol reaction of acetaldehyde [J].
Hayashi, Yujiro ;
Itoh, Takahiko ;
Aratake, Seiji ;
Ishikawa, Hayato .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (11) :2082-2084
[9]   Efficient proline-catalyzed Michael additions of unmodified ketones to nitro olefins [J].
List, B ;
Pojarliev, P ;
Martin, HJ .
ORGANIC LETTERS, 2001, 3 (16) :2423-2425
[10]  
Luo S., 2006, ANGEW CHEM, V118, P3165