4.8 Article

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

Journal

ORGANIC LETTERS
Volume 8, Issue 14, Pages 3077-3079

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol061053+

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Funding

  1. NCRR NIH HHS [P20 RR016480] Funding Source: Medline

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[GRAPHICS] 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.

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