Differentiation of diastereotopic bromine atoms in S_N2 reactions of gem-dibromides

摘要

A novel directed S_N2 reaction of conformationally biased gem-dibromides and an arenesulfinate anion is described. The reaction results in the diastereoselective formation of α-bromosulfones. The selectivity originates from pre-coordination of the nucleophile to a free hydroxyl group in the γ-position.