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01514 am a22002293u 4500 |
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82058 |
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|a Fujiwara, Yuji
|e author
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|a Massachusetts Institute of Technology. Department of Chemistry
|e contributor
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|a Fujiwara, Yuji
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|a Sun, Jianwei
|e contributor
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|a Fu, Gregory C.
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|a Sun, Jianwei
|e author
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|a Fu, Gregory C.
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|a Enantioselective carbon-sulfur bond formation: γ additions of aryl thiols to allenoates catalyzed by a chiral phosphepine
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|b Royal Society of Chemistry, The,
|c 2013-11-08T19:16:15Z.
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|z Get fulltext
|u http://hdl.handle.net/1721.1/82058
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|a 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.
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|a National Institute of General Medical Sciences (U.S.) (Grant R01-GM57034)
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|a en_US
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|a Article
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|t Chemical Science
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