Download PDF
Synlett 1995; 1995(10): 1027-1028
DOI: 10.1055/s-1995-5159
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 Highly Diastereoselective Epoxidation of N-Boc 2-Alkenyloxazolidines: Application in Asymmetric Synthesis

A. Agami, F. Couty* , O. Venier
  • *Laboratoire de Synthèse Asymétrique, Université P. et M. Curie, Case 47, 4 place Jussieu, 75005 Paris, France
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

N-Boc 2-alkenyloxazolidines derived from (R)-phenylglycinol underwent a highly diastereoselective bromocarbamoylation when treated with NBS. Reaction of the resulting bicyclic urethanes with sodium ethoxide yielded diastereomerically pure oxazolidine epoxides. This new methodology was applied to the enantioselective synthesis of the anti isomer of the taxol side chain methyl ester, i.e. (2R,3R)-N-benzoyl-3-phenylisoserine methyl ester.

oxazolidine - bromocarbamoylation - asymmetric epoxidation - taxol side chain