Download PDF
Synlett 1996; 1996(10): 1010-1012
DOI: 10.1055/s-1996-5648
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.

Consecutive Intramolecular Azomethine Ylid Cycloaddition - Pummerer Rearrangement as a Strategy for the Synthesis of Enantiomerically Pure 5-(Hydroxymethyl)prolines

L. M. Harwood* , I. A. Lilley
  • *Department of Chemistry, Reading University, Whiteknights, Reading RG6 6AD, U.K., Fax +44(118)9318449, e-mail l.m.harwood@reading.ac.uk
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

The thiatricycle (2S, 6R, 8S, 12S)-(2), prepared in one pot by reaction of (5S)-5-phenylmorpholinone with (prop-2-enyl)thioethanal, is converted stereoselectively to sulfoxide (5) which undergoes regio- and stereoselective Pummerer rearrangement. Subsequent elaboration furnishes (2S, 4R, 8S)-5-(hydroxymethyl)-4-methylproline (9).

chiral - azomethine - ylid - Pummerer - 5-(hydroxymethyl)proline