| Ab inito Study on Enantioselective Reduction of Ketones Catalyzed by Thiazolidino[3,4—c]oxazaborolidines |
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| 引用本文： | 李明,谢如刚,田安民.Ab inito Study on Enantioselective Reduction of Ketones Catalyzed by Thiazolidino[3,4—c]oxazaborolidines[J].中国化学,2002,20(10):983-989. |
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| 作者姓名： | 李明 谢如刚 田安民 |
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| 作者单位： | [1]DepartmentofChemistry,SichuanUniversity,Chengdu,Sichuan610064,china [2]DepartmentofChemistry,SouthwestNormalUniversity,Chongqing400715china |
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| 摘 要： | The ab initio molecular orbital method is employed to study the enantioselective reduction of acetophenone with borane catalyzed by thiszolidino3,4-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 atate 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-OCO6-membered ring.
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| 关 键 词： | 噻唑 [3 4－c]唑 Ab inito 量子化学 结构 |
Ab initio Study on Enantioselective Reduction of Ketones Catalyzed by Thiazolidino [3, 4‐c ] oxazaborolidines |
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| Ming Li,Ru‐Gang Xie,An‐Min Han.Ab initio Study on Enantioselective Reduction of Ketones Catalyzed by Thiazolidino [3, 4‐c ] oxazaborolidines[J].Chinese Journal of Chemistry,2002,20(10):983-989. |
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| Authors: | Ming Li Ru‐Gang Xie An‐Min Han |
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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. |
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| Keywords: | ab initio thiazolidino [3] 4‐c oxazaborolidine enantioselective reduction of acetophenone transition state |
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