Highly Diastereo- and Enantioselective Organocatalytic Michael Addition of α-Ketoamides to Nitroalkenes

被引：94

作者：

Basle, Olivier ^{[1
]}

Raimondi, Wilfried ^{[1
]}

Sanchez Duque, Maria del Mar ^{[1
]}

Bonne, Damien ^{[1
]}

Constantieux, Thierry ^{[1
]}

Rodriguez, Jean ^{[1
]}

机构：

[1] Aix Marseille Univ, CNRS, Ctr St Jerome, iSm2,UMR 6263,Serv 531, F-13397 Marseille, France

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 22期

关键词：

ASYMMETRIC CONJUGATE ADDITION; MANNICH-TYPE REACTIONS; DIRECT ALDOL REACTION; STEREOSELECTIVE-SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; POLYKETIDE SYNTHASES; NITROALDOL REACTION; BOND FORMATION; KETO ESTERS; NITROOLEFINS;

D O I：

10.1021/ol102289g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first organocatalytic enantio- and diastereoselective conjugate addition of alpha-ketoamides to nitroalkenes has been achieved using a bifunctional amino thiourea catalyst. In this new approach, the substrate amide proton plays a critical role in the formation of the Michael anti-adducts in high yields and high stereoselectivities. To illustrate the high synthetic potential of this methodology, the diastereo- and enantioselective synthesis of a hexasubstituted cyclohexane via a Michael-Michael-Henry cascade reaction is described.

引用

页码：5246 / 5249

页数：4

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