Diastereoselectivity in the Epoxidation of Substituted Cyclohexenes by Dimethyldioxirane(1)(,)(2).
Three series of compounds based on the cyclohexene framework have been epoxidized by dimethyldioxirane. A pronounced dependence of epoxide diastereoselectivity on substituent has been observed. In addition there is a solvent influence on this stereoselectivity. The results have been explained by invoking steric, H-bonding, and dipole-dipole influences on the epoxide stereochemistry.
Murray
Robert W.
RW
Department of Chemistry, University of Missouri-St. Louis, St. Louis, Missouri 63121.
Singh
Megh
M
Williams
Brian L.
BL
Moncrieff
Hazel M.
HM