Tetrahedron: Asymmetry

From 3-aza-2-oxobicyclo [3.1. 0] hexane to enantiopure disubstituted cyclopropane: a convenient approach to cis-2, 3-methano-GABA

R Galeazzi, G Mobbili, M Orena

Index: Galeazzi, Roberta; Mobbili, Giovanna; Orena, Mario Tetrahedron Asymmetry, 1997 , vol. 8, # 1 p. 133 - 137

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Citation Number: 37

Abstract

Starting from the diastereomerically pure 4-ethenyl pyrrolidin-2-one 5, through simple steps the mesyl derivative 8 was obtained, which underwent intramolecular alkylation to give, in good yield, the 3-aza-2-oxobicyclo [3.1. 0] hexane 9. This compound was subsequently converted into enantiomerically pure (−)-cis-2, 3-methano-GABA, 2.