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Highly stereoselective preparation of nitro olefins and nitro dienes by the addition-elimination of copper-zinc organometallics to [beta]-alkylthio and [beta]-phenylsulfonyl nitro olefins
dc.contributor.authorRetherford, Caroleen_US
dc.contributor.authorKnochel, Paulen_US
dc.date.accessioned2006-04-10T14:50:09Z
dc.date.available2006-04-10T14:50:09Z
dc.date.issued1991-01-21en_US
dc.identifier.citationRetherford, Carole, Knochel,, Paul (1991/01/21)."Highly stereoselective preparation of nitro olefins and nitro dienes by the addition-elimination of copper-zinc organometallics to [beta]-alkylthio and [beta]-phenylsulfonyl nitro olefins." Tetrahedron Letters 32(4): 441-444. <http://hdl.handle.net/2027.42/29500>en_US
dc.identifier.urihttp://www.sciencedirect.com/science/article/B6THS-42GDG81-7G/2/fd79795ccf11056fdfe7a096ac6e492fen_US
dc.identifier.urihttps://hdl.handle.net/2027.42/29500
dc.description.abstractThe addition-elimination of copper-zinc organometallics RCu(CN)ZnX to (E)-1-nitro-2-phenylsulfonyl ethylene 2a gave highly functionalized pure (E) nitro olefins and stereoselectively (1E, 3E) and (1E, 3Z)-1-nitrodienes in excellent yields. [beta]-Alkylthio nitro olefins such as 2-ethylthio-1-nitro-1-cyclohexene 2b and 2,2-dimethylthio-1-nitroethylene 12 were found to have a similar behavior. This methodology allowed an expeditive preparation of the triene 5 which underwent an extremely mild silica gel-catalyzed, stereospecific Diels-Alder cyclization.en_US
dc.format.extent359000 bytes
dc.format.extent3118 bytes
dc.format.mimetypeapplication/pdf
dc.format.mimetypetext/plain
dc.language.isoen_US
dc.publisherElsevieren_US
dc.titleHighly stereoselective preparation of nitro olefins and nitro dienes by the addition-elimination of copper-zinc organometallics to [beta]-alkylthio and [beta]-phenylsulfonyl nitro olefinsen_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelMaterials Science and Engineeringen_US
dc.subject.hlbsecondlevelChemistryen_US
dc.subject.hlbsecondlevelChemical Engineeringen_US
dc.subject.hlbsecondlevelBiological Chemistryen_US
dc.subject.hlbtoplevelEngineeringen_US
dc.subject.hlbtoplevelScienceen_US
dc.subject.hlbtoplevelHealth Sciencesen_US
dc.description.peerreviewedPeer Revieweden_US
dc.contributor.affiliationumWillard H. Dow Laboratories, Department of Chemistry, University of Michigan Ann Arbor, Michigan 8109 U.S.A.en_US
dc.contributor.affiliationumWillard H. Dow Laboratories, Department of Chemistry, University of Michigan Ann Arbor, Michigan 8109 U.S.A.en_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/29500/1/0000586.pdfen_US
dc.identifier.doihttp://dx.doi.org/10.1016/S0040-4039(00)79462-7en_US
dc.identifier.sourceTetrahedron Lettersen_US
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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