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Ionic Liquid-Supported (ILS) (S)-Pyrrolidine Sulfonamide for Asymmetric Michael addition reactions of Aldehydes with Nitroolefins.


Citation

Abdul Rahman, Mohd Basyaruddin and D. Headley, Allan and Dhungana, Kritanjali and M. Omar, Emmy (2011) Ionic Liquid-Supported (ILS) (S)-Pyrrolidine Sulfonamide for Asymmetric Michael addition reactions of Aldehydes with Nitroolefins. Letters in Organic Chemistry, 8 (3). pp. 170-175. ISSN 1570-1786; 1875-6255

Abstract / Synopsis

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.


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Additional Metadata

Item Type: Article
Divisions: Faculty of Science
Publisher: Bentham Science Publishers
Keywords: Asymmetric catalysis; Ionic liquid; Michael addition; Nitroolefins; Aldehydes; Cornerstone; Enantioselective; Organocatalytic; Methyl.
Depositing User: Nur Farahin Ramli
Date Deposited: 30 Jul 2013 16:43
Last Modified: 02 Oct 2015 10:22
URI: http://psasir.upm.edu.my/id/eprint/25057
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