Effect of the heteroatomic substituent on the pi-facial diastereoselectivity in Lewis acid catalyzed carbonyl ene reaction: A theoretical study

Quantum chemical investigation on the optimized transition structures of intermolecular ene reaction containing various heteroatomic substituents at the α-carbon atom reveal that, the electrostatic effect produced by the ene moiety plays a crucial role in controlling the conformation of the transition structure. The stereoselectivity calculated from the proposed model agreed nicely with the reported experimental results.