Enantioselective Organocatalytic Conjugate Addition of Aldehydes to Nitrodienes

被引：102

作者：

Belot, Sebastien ^{[1
]}

Massaro, Assunta ^{[1
]}

Tenti, Alice ^{[2
]}

Mordini, Alessandro ^{[2
]}

Alexakis, Alexandre ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

[2] CNR, Area Ric, Ist Chim Composti Organomet, I-50019 Florence, Italy

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 20期

关键词：

D O I：

10.1021/ol801772p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric organocatalyzed Michael addition of aldehydes to alpha,beta-gamma,delta-unsaturated nitro compounds has been accomplished using only 5 mol % of (S)-diphenylprolinol silyl ether and 2 equiv of aldehyde in a mixture of ethanol and water (5% v/v). The Michael adducts were obtained in good yields, diastereoselectivities up to 94/6, and ee's up to 99%. This process provides synthetically useful compounds which can easily lead to more complex molecules, as exemplified with substituted tetrahydropyran or cyclohexene.

引用

页码：4557 / 4560

页数：4

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