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Synlett 2000; 2000(4): 504-508
DOI: 10.1055/s-2000-6566
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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
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Publication Date:
31 December 2000 (online)

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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.

stereoselective alkylation - 5,5-trans-lactam ring - pyrrolidines/pyrrolidinones