4.8 Article

Sc(III)-Catalyzed Enantioselective Addition of Thiols to α,β-Unsaturated Ketones in Neutral Water

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ORGANIC LETTERS
卷 13, 期 9, 页码 2150-2152

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AMER CHEMICAL SOC
DOI: 10.1021/ol200379r

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  1. Minister dell'Istruzione, dell'Universita e della Ricerca (MIUR)
  2. Universita degli Studi di Perugia [RBFR08TTWW, RBFR08J78Q]

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This report concerns Lewis acid catalyzed enantioselective sulfa-Michael addition in neutral water by using a very efficient Sc(OTf)(3)/bipyridine 1 catalytic system. It is noteworthy that the protocol presented employs water as a reaction medium and allows us to obtain very high stereoselectivity and satisfactory yields for beta-keto sulphides deriving from aliphatic thiols. The recovery and reuse of both the aqueous medium and the catalytic system is also reported.

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