Fujiwara, Yuji and Sun, Jianwei and Fu, Gregory C. (2011) Enantioselective carbon–sulfur bond formation: γ additions of aryl thiols to allenoates catalyzed by a chiral phosphepine. Chemical Science, 2 (11). pp. 2196-2198. ISSN 2041-6520. PMCID PMC3248350. doi:10.1039/c1sc00414j. https://resolver.caltech.edu/CaltechAUTHORS:20200512-133335212
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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.
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| Additional Information: | © 2011 The Royal Society of Chemistry. Received 29th June 2011, Accepted 1st August 2011, First published on 25th August 2011. Support was provided by the National Institute of Health (National Institute of General Medical Sciences, grant R01-GM57034) and Dainippon Sumitomo Pharma Co., Ltd. (fellowship for Y.F.). We thank Dr Jonathan E. Wilson for a preliminary study. | |||||||||
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| Issue or Number: | 11 | |||||||||
| PubMed Central ID: | PMC3248350 | |||||||||
| DOI: | 10.1039/c1sc00414j | |||||||||
| Record Number: | CaltechAUTHORS:20200512-133335212 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20200512-133335212 | |||||||||
| Official Citation: | Enantioselective carbon–sulfur bond formation: γ additions of aryl thiols to allenoates catalyzed by a chiral phosphepine. Chem. Sci., 2011, 2, 2196-2198; doi: 10.1039/c1sc00414j | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 103148 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Tony Diaz | |||||||||
| Deposited On: | 12 May 2020 20:39 | |||||||||
| Last Modified: | 16 Nov 2021 18:18 |
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