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

• 来源期刊: 中国化学（英文版）
• 年，卷（期）: 2002,（10）
• 页码范围: 983-989
• 页数: 7页
• 语种: 英文

摘要

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 result 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.