Ionic Liquid-Supported (ILS) (S)-Pyrrolidine Sulfonamide for Asymmetric Michael Addition Reactions of Aldehydes with Nitroolefins

被引：0
|
作者：
Omar, Emmy M. [2 ]
Dhungana, Kritanjali [1 ]
Headley, Allan D. [1 ]
Rahman, Mohd Basyaruddin Abdul [2 ]
机构：
[1] Texas A&M Univ, Dept Chem, Commerce, TX 75429 USA
[2] Univ Putra Malaysia, Dept Chem, Fac Sci, Upm Serdang 43400, Selangor, Malaysia
来源：
LETTERS IN ORGANIC CHEMISTRY | 2011年 / 8卷 / 03期
关键词：
Aldehydes; asymmetric catalysis; ionic liquid; michael addition; nitroolefins; EFFICIENT ORGANOCATALYSTS; CONJUGATE ADDITION; KETONES; CATALYSTS; NITROALKENES; STRATEGY; PROLINE;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A class of ionic liquid supported (ILS) (S)-pyrrolidine sulfonamide organocatalyst (1c), which was developed earlier in our lab, has been applied to a wider range of Michael addition reaction, involving various aryl-substituted nitroolefins and a series of aldehydes. Catalyst 1c catalyzes Michael additions in which only 2 equivalents of aldehydes to each equivalent of nitroolefin are required. With 10 mol% of ILS catalyst 1c loading, moderate to excellent yields (51-98%) with moderate enantioselectivities (28-83% ee) and high diastereoselectivities (syn/anti ratio up to 97/3) were obtained. Moreover, the catalyst 1c could be easily recycled and reused for at least 5 times with slightly reduced activities.
引用
收藏
页码：170 / 175
页数：6
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