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Palladium‐Catalyzed Alkene Carboamination Reactions of Electron‐Poor Nitrogen Nucleophiles
dc.contributor.authorPeterson, Luke J.en_US
dc.contributor.authorWolfe, John P.en_US
dc.date.accessioned2015-08-05T16:47:22Z
dc.date.available2016-08-08T16:18:39Zen
dc.date.issued2015-07-06en_US
dc.identifier.citationPeterson, Luke J.; Wolfe, John P. (2015). "Palladium‐Catalyzed Alkene Carboamination Reactions of Electron‐Poor Nitrogen Nucleophiles." Advanced Synthesis & Catalysis 357(10): 2339-2344.en_US
dc.identifier.issn1615-4150en_US
dc.identifier.issn1615-4169en_US
dc.identifier.urihttps://hdl.handle.net/2027.42/112250
dc.description.abstractModified reaction conditions that facilitate Pd‐catalyzed alkene carboamination reactions of electron‐deficient nitrogen nucleophiles are reported. Pent‐4‐enylamine derivatives bearing N‐tosyl or N‐trifluoroacetyl groups are coupled with aryl triflates to afford substituted pyrrolidines in good yield. These reactions proceed via a mechanism involving anti‐aminopalladation of the alkene, which differs from previously reported analogous reactions of N‐aryl‐ and N‐Boc‐pentenylamines. The application of these conditions to a formal synthesis of (±)‐aphanorphine is also described.en_US
dc.publisherWILEY‐VCH Verlagen_US
dc.subject.otherpalladiumen_US
dc.subject.otheralkenesen_US
dc.subject.otheraryl halidesen_US
dc.subject.otherheterocyclesen_US
dc.titlePalladium‐Catalyzed Alkene Carboamination Reactions of Electron‐Poor Nitrogen Nucleophilesen_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelChemistryen_US
dc.subject.hlbtoplevelScienceen_US
dc.description.peerreviewedPeer Revieweden_US
dc.contributor.affiliationumUniversity of Michigan, Department of Chemistry, 930 N. University Ave., Ann Arbor, MI, 48109‐1055, USAen_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/112250/1/2339_ftp.pdf
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/112250/2/adsc_201500334_sm_miscellaneous_information.pdf
dc.identifier.doi10.1002/adsc.201500334en_US
dc.identifier.sourceAdvanced Synthesis & Catalysisen_US
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dc.owningcollnameInterdisciplinary and Peer-Reviewed


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