PDF herunterladen
Synlett 2000; 2000(2): 236-238
DOI: 10.1055/s-2000-6494
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 Rapid Approach to Amino-Acid Derivatives by [2,3]-Stevens Rearrangement

Amélie P. A. Arboré* , Daniel J. Cane-Honeysett, Iain Coldham, Mark L. Middleton
  • *School of Chemistry, University of Exeter, Stocker Road, Exeter, UK EX4 4QD; Fax +44 13 92 26 34 34; E-mail: I.Coldham@exeter.ac.uk
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

Allylation of amino-acid esters gives rise to intermediate quaternary ammonium salts, which undergo proton abstraction to give ylides and [2,3]-sigmatropic rearrangement. The resulting α-amino-acid derivatives can be subjected to N-deallylation to provide a rapid access to α-allyl-α-amino-esters. Using N-benzyl proline methyl ester, chirality transfer from carbon to nitrogen then back to carbon takes place.

amines - amino acids - rearrangements - ylides - chirality transfer