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Issue 11, 2011
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Enantioselective carbon–sulfur bond formation: γ additions of aryl thiols to allenoates catalyzed by a chiral phosphepine

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Abstract

An effective phosphine-catalyzed method was developed for the enantioselective addition of aryl thiols to the γ position of allenoates, thereby providing ready access to aryl alkyl sulfides in very good ee. The array of mechanistic data are consistent with the addition of the chiral phosphine to the allenoate being the turnover-limiting step of the catalytic cycle. The optimized reaction conditions, as well as the mechanistic observations, differ markedly from an earlier report on asymmetric additions of alkylthiols to allenoates, which highlights the potential for divergent behavior between alkyl and aryl thiols when acting as nucleophiles.

Graphical abstract: Enantioselective carbon–sulfur bond formation: γ additions of aryl thiols to allenoates catalyzed by a chiral phosphepine

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Publication details

The article was received on 29 Jun 2011, accepted on 01 Aug 2011 and first published on 25 Aug 2011


Article type: Edge Article
DOI: 10.1039/C1SC00414J
Citation: Chem. Sci., 2011,2, 2196-2198
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    Enantioselective carbon–sulfur bond formation: γ additions of aryl thiols to allenoates catalyzed by a chiral phosphepine

    Y. Fujiwara, J. Sun and G. C. Fu, Chem. Sci., 2011, 2, 2196
    DOI: 10.1039/C1SC00414J

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