Abstract
Addition of 5-substituted dithianyl anions to carbonyl compounds normally produces trans adducts. The presence of a nucleophilic hydroxymethyl group in position 5 dramatically decreases the trans stereoselectivity of the reaction in THF. The trans/cis ratio shows a bell curve dependence on HMPA, fitted to a quantitative model involving a series of equilibrated ion pairs, of which an intermediate contact ion pair possessing three (effective) HMPA molecules yields the trans adduct with much higher stereoselectivity. [structure: see text]
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