Synlett 2000; 2000(4): 504-508
DOI: 10.1055/s-2000-6566
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.

Stereoselective Synthesis of α-Methyl and β-Methyl Pyrrolidine 5,5-trans-Lactam (5-Oxo-hexahydro-pyrrolo[3,2-b]pyrrole) and Stereoselective Alkylation of the Strained Pyrrolidine 5,5-Trans-Lactam Ring System

Alan D. Borthwick* , Andrew J. Crame, David E. Davies, Anne M. Exall, Deborah L. Jackson, Andrew M. Mason, Andrew M. K. Pennell, Gordon G. Weingarten
  • *Department of Enzyme Medicinal Chemistry II, Glaxo Wellcome Research and Development, Medicines Research Centre, Gunnels Wood Road, Stevenage, Herts SG1 2NY, UK; Fax +44 (0) 14 38 76 36 16; E-mail: adb3028@ggr.co.uk
Further Information

Publication History

Publication Date:
31 December 2000 (online)

The α-methyl pyrrolidine 5,5-trans-lactam 11 was prepared by stereoselective alkylation of the strained pyrrolidine 5,5-trans-lactam ring system. This stereoselective functionalisation also occurs with a wide range of different electrophiles giving the analogous α-substituted trans-lactams. The corresponding β-methyl pyrrolidine 5,5-trans-lactam was prepared by stereoselective methylation prior to ring closure.