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Letters in Organic Chemistry


ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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 and Mohd Basyaruddin Abdul Rahman

Volume 8, Issue 3, 2011

Page: [170 - 175] Pages: 6

DOI: 10.2174/157017811795038395

Price: $65


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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