Abstract
Effect of remote polar substituents on the pi-diastereofacial selectivity of Lewis acid catalyzed carbonyl ene reaction has been investigated. Quantum chemical investigations using B3LYP/6-31G∗ level of theory on various substrates where the carbonyl group resides in an isosteric environment revealed that electrostatic effect plays a crucial role in determining the relative energies of the corresponding transition structures (TS) of the carbonyl ene reaction. This fact is nicely reflected in the product diastereoselectivities of various model carbonyl ene reactions.
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