dc.contributor.author | Cordier, Christopher J. | |
dc.contributor.author | Fu, Gregory C. | |
dc.contributor.author | Binder, Jorg T. | |
dc.date.accessioned | 2013-11-08T18:20:49Z | |
dc.date.available | 2013-11-08T18:20:49Z | |
dc.date.issued | 2012-10 | |
dc.date.submitted | 2012-08 | |
dc.identifier.issn | 0002-7863 | |
dc.identifier.issn | 1520-5126 | |
dc.identifier.uri | http://hdl.handle.net/1721.1/82054 | |
dc.description.abstract | We 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.sponsorship | National Institute of General Medical Sciences (U.S.) (Grant R01-GM62871) | en_US |
dc.language.iso | en_US | |
dc.publisher | American Chemical Society (ACS) | en_US |
dc.relation.isversionof | http://dx.doi.org/10.1021/ja308460z | en_US |
dc.rights | Article 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.source | PMC | en_US |
dc.title | Catalytic Enantioselective Cross-Couplings of Secondary Alkyl Electrophiles with Secondary Alkylmetal Nucleophiles: Negishi Reactions of Racemic Benzylic Bromides with Achiral Alkylzinc Reagents | en_US |
dc.type | Article | en_US |
dc.identifier.citation | Binder, 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.department | Massachusetts Institute of Technology. Department of Chemistry | en_US |
dc.contributor.mitauthor | Binder, Jorg T. | en_US |
dc.contributor.mitauthor | Cordier, Christopher J. | en_US |
dc.contributor.mitauthor | Fu, Gregory C. | en_US |
dc.relation.journal | Journal of the American Chemical Society | en_US |
dc.eprint.version | Author's final manuscript | en_US |
dc.type.uri | http://purl.org/eprint/type/JournalArticle | en_US |
eprint.status | http://purl.org/eprint/status/PeerReviewed | en_US |
dspace.orderedauthors | Binder, Jörg T.; Cordier, Christopher J.; Fu, Gregory C. | en_US |
mit.license | PUBLISHER_POLICY | en_US |
mit.metadata.status | Complete | |