Ab. Charette et B. Cote, CARBOHYDRATES AS CHIRAL AUXILIARIES - THE ASYMMETRIC EPOXIDATION REACTION OF OLEFINS, Tetrahedron : asymmetry, 4(11), 1993, pp. 2283-2286
Under optimized conditions, the epoxidation of -2-butenyl-3,4,6-tri-O-
benzyl-beta-D-glucopyranose gave a 9:1 mixture of diastereomers. The d
iastereoselectivities observed were shown to be highly dependent on th
e nature of the reagent used and of the protecting group at C-2 of the
auxiliary.