Bronsted Acid Catalyzed Highly Diastereoselective Michael-Type Addition of Azlactones to Enones

被引：24

作者：

Avila, Eloah P. ^{[1
]}

de Mello, Amanda C. ^{[1
]}

Diniz, Renata ^{[1
]}

Amarante, Giovanni W. ^{[1
]}

机构：

[1] Univ Fed Juiz de Fora, Dept Chem, BR-36036900 Juiz De Fora, MG, Brazil

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 10期

关键词：

Organocatalysis; Michael addition; Diastereoselectivity; Regioselectivity; Enones; ENANTIOSELECTIVE ORGANOCATALYTIC ADDITION; ASYMMETRIC-SYNTHESIS; AMINO-ACIDS; IN-SITU; CYCLIZATION; PROTONATION; REGIO;

D O I：

10.1002/ejoc.201300076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly regio- and diastereoselective 1,4-addition of azlact-ones to enones catalyzed by a Bronsted acid is described. The Michael adducts were prepared in moderate to good yields and with complete control of the relative stereochemistry. In addition, two consecutive stereogenic centers were created, one of which was a quaternary stereocenter. The method was successfully extended to the first highly diastereoselective desymmetrization of dibenzylidene acetone.

引用

页码：1881 / 1883

页数：3

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