Ab initio Study on Enantioselective Reduction of Ketones Catalyzed by Thiazolidino [3, 4‐c ] oxazaborolidines

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Abstract
The ab initio molecular orbital method is employed to study the enantioselective reduction of acetophenone with borane catalyzed by thiazolidino [3, 4‐c] oxazaborolidine. Computation resuit shows that the controlling step for the reduction is the decomposition of the catalyst‐alkoxyborane adduct and the reduction leads to S‐alcohols. The transition state of the hydride transfer from the borane moiety to the carbonyl carbon of acetophenone is a twisted chair structure with a B (2)—N (3)—BBH3—HBH3—CCO—OCO 6‐membered ring.