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

Author(s): Emmy M. Omar , Kritanjali Dhungana , Allan D. Headley , Mohd Basyaruddin Abdul Rahman .

Journal Name: Letters in Organic Chemistry

Volume 8 , Issue 3 , 2011

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Abstract:

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.

Keywords: Aldehydes, asymmetric catalysis, ionic liquid, michael addition, nitroolefins, cornerstone, enantioselective, organocatalytic, methyl

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Article Details

VOLUME: 8
ISSUE: 3
Year: 2011
Page: [170 - 175]
Pages: 6
DOI: 10.2174/157017811795038395
Price: $58

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