Enantioselective Michael Addition of Nitroalkanes to Nitroalkenes Catalyzed by Chiral Bifunctional Quinine-Based Squaramides

被引：27

作者：

Kanberoglu, Esra ^{[1
]}

Tanyeli, Cihangir ^{[1
]}

机构：

[1] Middle E Tech Univ, Dept Chem, TR-06800 Ankara, Turkey

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 5卷 / 01期

关键词：

asymmetric catalysis; enantioselectivity; Michael addition; nitro compounds; organocatalysis; CONJUGATE ADDITION; ORGANOCATALYSTS;

D O I：

10.1002/ajoc.201500339

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A family of chiral bifunctional acid-/base-type quinine/squaramide organocatalysts is shown to be highly active promoters of the conjugate addition of 1-nitropropane to various trans--nitroalkenes. The cooperation of the quinine and the sterically encumbered squaramide moieties catalyzed the Michael addition reactions at 0 degrees C by using a catalyst loading of only 2mol% to afford the 1,3-dinitro Michael adducts with excellent enantioselectivity and diastereoselectivity (up to 95%ee and syn/anti isomers up to 96:4).

引用

页码：114 / 119

页数：6

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