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dc.contributor.authorCordier, Christopher J.
dc.contributor.authorFu, Gregory C.
dc.contributor.authorBinder, Jorg T.
dc.date.accessioned2013-11-08T18:20:49Z
dc.date.available2013-11-08T18:20:49Z
dc.date.issued2012-10
dc.date.submitted2012-08
dc.identifier.issn0002-7863
dc.identifier.issn1520-5126
dc.identifier.urihttp://hdl.handle.net/1721.1/82054
dc.description.abstractWe have developed a nickel-catalyzed method for the asymmetric cross-coupling of secondary electrophiles with secondary nucleophiles, specifically, stereoconvergent Negishi reactions of racemic benzylic bromides with achiral cycloalkylzinc reagents. In contrast to most previous studies of enantioselective Negishi cross-couplings, tridentate pybox ligands are ineffective in this process; however, a new, readily available bidentate isoquinoline–oxazoline ligand furnishes excellent ee’s and good yields. The use of acyclic alkylzinc reagents as coupling partners led to the discovery of a highly unusual isomerization that generates a significant quantity of a branched cross-coupling product from an unbranched nucleophile.en_US
dc.description.sponsorshipNational Institute of General Medical Sciences (U.S.) (Grant R01-GM62871)en_US
dc.language.isoen_US
dc.publisherAmerican Chemical Society (ACS)en_US
dc.relation.isversionofhttp://dx.doi.org/10.1021/ja308460zen_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.titleCatalytic Enantioselective Cross-Couplings of Secondary Alkyl Electrophiles with Secondary Alkylmetal Nucleophiles: Negishi Reactions of Racemic Benzylic Bromides with Achiral Alkylzinc Reagentsen_US
dc.typeArticleen_US
dc.identifier.citationBinder, Jorg T., Christopher J. Cordier, and Gregory C. Fu. “Catalytic Enantioselective Cross-Couplings of Secondary Alkyl Electrophiles with Secondary Alkylmetal Nucleophiles: Negishi Reactions of Racemic Benzylic Bromides with Achiral Alkylzinc Reagents.” Journal of the American Chemical Society 134, no. 41 (October 17, 2012): 17003-17006.en_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Chemistryen_US
dc.contributor.mitauthorBinder, Jorg T.en_US
dc.contributor.mitauthorCordier, Christopher J.en_US
dc.contributor.mitauthorFu, Gregory C.en_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.orderedauthorsBinder, Jörg T.; Cordier, Christopher J.; Fu, Gregory C.en_US
mit.licensePUBLISHER_POLICYen_US
mit.metadata.statusComplete


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