Highly enantioselective aldehyde-nitroolefin Michael addition reactions catalyzed by recyclable fluorous (S) diphenylpyrrolinol silyl ether |
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Authors: | Liansuo Zu Jian Wang Wei Wang |
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Affiliation: | a Department of Chemistry, University of New Mexico, Albuquerque, NM 87131-0001, USA b School of Pharmacy, East China University of Science and Technology, Shanghai 200237, PR China |
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Abstract: | A recyclable and reusable (S) diphenylpyrrolinol silyl ether I organocatalyst bearing a n-C8F17 fluorous tag has been demonstrated for promoting the asymmetric Michael addition reactions of a wide range of aldehydes with both aryl and alkyl-substituted nitroolefins and excellent levels of enantio- and diastereoselectivities are achieved. The catalyst I can be conveniently recovered by fluorous solid-phase extraction and subsequently reused (up to eight cycles) without significant loss of its catalytic activity and stereoselectivity for the process. |
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Keywords: | Asymmetric organocatalysis Diphenylpyrrolinol silyl ether Fluorous chemistry Michael addition reaction Nitroolefin |
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