PDF herunterladen
Synlett 1997; 1997(6): 725-727
DOI: 10.1055/s-1997-3248
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

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