Organic Letters 2006-07-06

A recyclable fluorous (S)-pyrrolidine sulfonamide promoted direct, highly enantioselective Michael addition of ketones and aldehydes to nitroolefins in water.

Liansuo Zu, Jian Wang, Hao Li, Wei Wang

Index: Org. Lett. 8 , 3077-3079, (2006)

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Abstract

[reaction: see text] A recycle and reusable fluorous (S)-pyrrolidine sulfonamide organocatalyst has been developed for promoting highly enantio- and diastereoselective Michael addition reactions of ketones and aldehydes with nitroolefins in water. The organocatalyst is conveniently recovered from the reaction mixtures by fluorous solid-phase extraction and can be subsequently reused (up to six cycles) without a significant loss of catalytic activity and stereoselectivity.