Stereocontrolled formation of epoxy peroxide functionality appended to a lactam ring

C M Marson; A Khan; R A Porter

doi:10.1021/jo001313f

Stereocontrolled formation of epoxy peroxide functionality appended to a lactam ring

J Org Chem. 2001 Jul 13;66(14):4771-5. doi: 10.1021/jo001313f.

Authors

C M Marson¹, A Khan, R A Porter

Affiliation

¹ Department of Chemistry, Queen Mary and Westfield College, University of London, London E1 4NS, UK. c.m.marson@uc.ac.uk

PMID: 11442402
DOI: 10.1021/jo001313f

Abstract

The action of tert-butyl hydroperoxide and tin(IV) chloride upon allylic alcohols containing a lactam ring leads mainly to epoxy alkyl peroxides with high diastereoselection. Both the stereochemistry and the products formed are in marked contrast to the reactions of the analogous carbocyclic allylic alcohols with tert-butyl hydroperoxide-VO(acac)2.