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Synlett 1997; 1997(6): 725-727
DOI: 10.1055/s-1997-3248
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A Tandem Amino-Cope Rearrangement/Enamine Alkylation Reaction

Steven M. Allin1 , Martin A. C. Button2 , Stephen J. Shuttleworth3
  • 1Department of Chemistry, Loughborough University, Loughborough, Leicestershire, LE11 3TU, England, EMAIL: s.m.allin@lboro.ac.uk; FAX: 44 (0)1509 223925
  • 2Department of Chemical & Biological Sciences, The University of Huddersfield, Queensgate, Huddersfield, HD1 3DH, England
  • 3GlycoDesign Inc., Suite 900, 480 University Ave., Toronto, Ontario, Canada
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Publication History

Publication Date:
31 December 2000 (online)

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Thermally induced [3,3]-sigmatropic rearrangement of 3-amino-1,5-diene substrates occurs to give the corresponding enamine products in high yield and with excellent trans:cis enamine selectivity. The enamine produced during the amino-Cope rearrangement has been directly derivatized, representing the first report of a tandem amino-Cope rearrangement/enamine alkylation reaction. The potential of this novel synthetic strategy is outlined.

sigmatropic rearrangement - enamine alkylation