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■ Stereochemical and Hydrogenolysis Studies with Substituted Isoxazolidines

John Palmer, John L. Roberts, Peter S. Rutledge,* and Paul D. Woodgate

*Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand

Abstract

The use of ¹³C n.m.r. and ¹H - ¹³C decoupling to assign the chemical shifts to protons geminal to substituents at the 3,4 and 5 positions of a pair of stereoisomeric isoxazolidines allows determination of the ring stereochemistries. Catalytic hydrogenation of N-phenylisoxazolidines with a 5-methoxycarbonyl group leads readily to azolidin-2-ones, but C-N hydrogenolysis is not achieved if there is a dimethoxyphenyl substituent at the 3 position of the isoxazolidine.