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Synthesis 2011(12): 1993-1997  
DOI: 10.1055/s-0030-1260465
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel Recyclable Organocatalytic System for the Highly Asymmetric Michael Addition of Aldehydes to Nitroolefins in Water

Dhruba Sarkar, Ramesh Bhattarai, Allan D. Headley*, Bukuo Ni*
Department of Chemistry, Texas A & M University-Commerce, Commerce, Texas 75429-3011, USA
Fax: +1(903)4686020; e-Mail: allan_headley@tamu-commerce.edu; e-Mail: bukuo_ni@tamu-commerce.edu;
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Publication History

Received 9 March 2011
Publication Date:
13 May 2011 (online)

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Abstract

A novel strategy for the asymmetric Michael addition of aldehydes to nitroolefins with a catalytic system of organocatalyst 1 in combination with ionic-liquid-supported (ILS) benzoic acid in water has been developed. The Michael adducts of this system give excellent diastereo- and enantioselectivities. A notable feature of this organocatalytic system is that the catalyst can be recycled more than 12 times without significant loss of enantioselectivity. In addition, the synthetic methodology presented is simple, practical, and environmentally benign.

Key words

aldehydes - asymmetric catalysis - green chemistry - ionic liquids - Michael addition

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