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dc.contributor.authorFujiwara, Yuji
dc.contributor.authorFu, Gregory C.
dc.date.accessioned2013-11-06T21:27:25Z
dc.date.available2013-11-06T21:27:25Z
dc.date.issued2011-08
dc.date.submitted2011-05
dc.identifier.issn0002-7863
dc.identifier.issn1520-5126
dc.identifier.urihttp://hdl.handle.net/1721.1/82012
dc.description.abstractThrough the design and synthesis of a new chiral phosphepine, the first catalytic asymmetric method for the [3 + 2] cycloaddition of allenes with olefins has been developed that generates cyclopentenes that bear nitrogen-, phosphorus-, oxygen-, and sulfur-substituted quaternary stereocenters. A wide array of racemic γ-substituted allenes can be employed in this stereoconvergent process, which occurs with good enantioselectivity, diastereoselectivity, regioselectivity, and yield. Mechanistic studies, including a unique observation of a (modest) kinetic resolution of a racemic allene, are consistent with addition of the phosphepine to the allene being the turnover-limiting step of the catalytic cycle.en_US
dc.description.sponsorshipNational Institute of General Medical Sciences (U.S.) (grant R01-GM57034)en_US
dc.description.sponsorshipDainippon Pharmaceutical Co., Ltd. (Fellowship)en_US
dc.language.isoen_US
dc.publisherAmerican Chemical Societyen_US
dc.relation.isversionofhttp://dx.doi.org/10.1021/ja2049012en_US
dc.rightsArticle is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.en_US
dc.sourcePMCen_US
dc.titleApplication of a New Chiral Phosphepine to the Catalytic Asymmetric Synthesis of Highly Functionalized Cyclopentenes That Bear an Array of Heteroatom-Substituted Quaternary Stereocentersen_US
dc.typeArticleen_US
dc.identifier.citationFujiwara, Yuji, and Gregory C. Fu. “Application of a New Chiral Phosphepine to the Catalytic Asymmetric Synthesis of Highly Functionalized Cyclopentenes That Bear an Array of Heteroatom-Substituted Quaternary Stereocenters.” Journal of the American Chemical Society 133, no. 31 (August 10, 2011): 12293-12297.en_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Chemistryen_US
dc.contributor.mitauthorFu, Gregory C.en_US
dc.contributor.mitauthorFujiwara, Yujien_US
dc.relation.journalJournal of the American Chemical Societyen_US
dc.eprint.versionAuthor's final manuscripten_US
dc.type.urihttp://purl.org/eprint/type/JournalArticleen_US
eprint.statushttp://purl.org/eprint/status/PeerRevieweden_US
dspace.orderedauthorsFujiwara, Yuji; Fu, Gregory C.en_US
mit.licensePUBLISHER_POLICYen_US
mit.metadata.statusComplete


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