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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