Enantioselective carbon–sulfur bond formation: γ additions of aryl thiols to allenoates catalyzed by a chiral phosphepine
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Fu_Enantioselective carbon.pdf
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Author(s)
Fujiwara, Yuji
Sun, Jianwei
Fu, Gregory C.
Date Issued
August 2011
Journal
Chemical Science
Publisher
Royal Society of Chemistry, The
Citation
Fujiwara, Yuji, Jianwei Sun, and Gregory C. Fu. “Enantioselective carbon–sulfur bond formation: γ additions of aryl thiols to allenoates catalyzed by a chiral phosphepine.” Chemical Science 2, no. 11 (2011): 2196.
Version
Author's final manuscript
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 alkyl thiols to allenoates, which highlights the potential for divergent behavior between alkyl and aryl thiols when acting as nucleophiles.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1039/c1sc00414j
