Stereospecificity in Diels–Alder reactions of dienes and dienophiles derived from methyl 4,6-O-benzylidene-α-D-glucopyranoside

Abstract

Conjugated enals (1) and (2) and dienes (3) and (4) derived from methyl 4,6-O-benzylidene-α-D-glucopyranoside underwent highly efficient (yields ranging from 75 to 95%) Diels–Alder reaction with complete facial specificity with butadiene, dimethyl acetylenedicarboxylate, and maleic anhydride leading exclusively to endo adducts with the latter.