Peptide-Catalyzed Conjugate Addition Reactions of Aldehydes to Nitroolefins

被引：26
作者：
Wiesner, Markus [1 ]
Wennemers, Helma [1 ]
机构：
[1] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland
来源：
SYNTHESIS-STUTTGART | 2010年 / 09期
基金：
瑞士国家科学基金会;
关键词：
asymmetric catalysis; conjugate addition reactions; organocatalysis; peptides; proline; ASYMMETRIC MICHAEL ADDITION; ENANTIOSELECTIVE MICHAEL; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; 1,4-ADDITION REACTIONS; GAMMA(2)-AMINO ACIDS; ENAMINE CATALYSIS; SILYL ETHERS; EFFICIENT; NITROALKENES; ORGANOCATALYSTS;
D O I：
10.1055/s-0029-1218651
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The tripeptide H-D-Pro-Pro-Glu-NH2 is an efficient catalyst for conjugate addition reactions of aldehydes to nitroolefins. Chiral gamma-nitroaldehydes are obtained in excellent yields and stereoselectivities in the presence of as little as 1 mol% of the tripeptide catalyst. Under further optimized reaction conditions the product was obtained in essentially perfect stereoselectivity (syn/anti, >99:1, 99% ee).
引用
收藏
页码：1568 / 1571
页数：4
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