Download PDF
Synlett 2001; 2001(12): 1836-1840
DOI: 10.1055/s-2001-18762
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.

An Acetone-derived Chiral Stabilised Azomethine Ylid: Synthesis of Enantiomerically Pure 5,5,-Dimethylproline Derivatives

David J. Aldous* , Michael G. B. Drew, Estelle M.-N. Hamelin, Laurence M. Harwood, Archie B. Jahans, Sukanthini Thurairatnam
  • *Rhône Poulenc Rorer Limited, Rainham Road South, Dagenham, Essex RM10 7XS, UK; Fax: + 44 (118) 9316782; E-mail: l.m.harwood@reading.ac.uk
Further Information

Publication History

Publication Date:
04 December 2001 (online)

 PDF Download  Permissions and Reprints All articles of this category

The chiral stabilised azomethine ylid 3 generated in situ via Lewis acid catalysed condensation of (5S)-5-phenylmorpholin-2-one with 2,2-dimethoxypropane can be trapped diastereoselectively with singly and doubly activated dipolarophiles. The cycloadducts may be dismantled in one pot to furnish enantiomerically pure 5,5-dimethylproline derivatives.

ketone-derived chiral stabilised azomethine ylid - 5,5-dimethylprolines - Lewis acid