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Generation of 2-azapentadienyl anions and their cycloaddition with alkenes. Synthesis of 2-alkenylpyrrolidines
dc.contributor.authorPearson, William H.en_US
dc.contributor.authorJacobs, Valerie A.en_US
dc.date.accessioned2006-04-10T17:53:48Z
dc.date.available2006-04-10T17:53:48Z
dc.date.issued1994-09-19en_US
dc.identifier.citationPearson,, William H., Jacobs, Valerie A. (1994/09/19)."Generation of 2-azapentadienyl anions and their cycloaddition with alkenes. Synthesis of 2-alkenylpyrrolidines." Tetrahedron Letters 35(38): 7001-7004. <http://hdl.handle.net/2027.42/31324>en_US
dc.identifier.urihttp://www.sciencedirect.com/science/article/B6THS-42M7V15-8P/2/8d8f5318d041cc128292a223df79a390en_US
dc.identifier.urihttps://hdl.handle.net/2027.42/31324
dc.description.abstract[alpha],[beta]-Unsaturated imines 2 bearing an N-[1-(tri-n-butylstannyl)]alkyl group were transmetalated with n-BuLi to generate 2-azapentadienyl anions 3 which underwent [4[pi]s+2[pi]s] anionic cycloadditions with alkenes to afford 2-alkenylpyrrolidines 4 after workup with an electrophile. The alkenyl group could be oxidized to a diol, aldehyde, or ester. The imine 2 was found to undergo a [1,5]-sigmatropic rearrangement of the tri-n-butylstannyl group at 80 [deg]C to provide the 2-azabutadiene 5.en_US
dc.format.extent309926 bytes
dc.format.extent3118 bytes
dc.format.mimetypeapplication/pdf
dc.format.mimetypetext/plain
dc.language.isoen_US
dc.publisherElsevieren_US
dc.titleGeneration of 2-azapentadienyl anions and their cycloaddition with alkenes. Synthesis of 2-alkenylpyrrolidinesen_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.affiliationumDepartment of Chemistry, University of Michigan, Ann Arbor, MI, USA.en_US
dc.contributor.affiliationumDepartment of Chemistry, University of Michigan, Ann Arbor, MI, USA.en_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/31324/1/0000233.pdfen_US
dc.identifier.doihttp://dx.doi.org/10.1016/0040-4039(94)88209-6en_US
dc.identifier.sourceTetrahedron Lettersen_US
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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