Stereocontrolled formation of epoxy peroxide functionality appended to a lactam ring.
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.
Marson
C M
CM
Department of Chemistry, Queen Mary and Westfield College, University of London, London E1 4NS, UK. c.m.marson@uc.ac.uk
Khan
A
A
Porter
R A
RA