Quantum chemical AM1 study of dimerization by hetero-Diels–Alder reaction of methyl 4,6-O-benzylidene-3-deoxy-3-C-methylene-α-D-hexopyranoside-2-ulose

Abstract

An unusual reaction, the dimerization by hetero-Diels–Alder reaction of methyl 4,6-O-benzylidene-3-deoxy-3-C-methylene-α-D-hexapyranoside-2-ulose, has been studied by a detailed computational analysis using the AM1 method. A reaction mechanism is proposed based on the calculated results, and it is in good agreement with the experimental data. The theoretical calculations can explain the excellent regioselectivity of this dimerization and other phenomena observed during the experiments.