| Studies on the Oxazaborolidine-catalyzed Enantioselective Reduction of 3-Morpholin-4-yl-1-phenyl-1-propanone with Density Functional Theory |
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| 作者姓名： | FAN Jian-Fen② LU Yun-Xiang WANG Qiu-Xia WU Li-Fen SUN Yun-Peng |
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| 作者单位： | Department of Chemistry，Suzhou University，Suzhou 215006，China |
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| 基金项目： | Project supported by the Research Foundation of Suzhou University (Q3109306) |
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| 摘 要： | Density functional theory (DFT) has been applied to study the enantioselective reduction of 3-morpholin-4-yl-l-phenyl-l-propanone with borane catalyzed by (S)-4-benzyl-5,5-diphenyl-l,3,2-oxazaborolidine at the B3LYP/6-31G* level. All molecular species involved in the four reaction steps have been fully optimized and the structural parameters are provided, and the micro process of reaction was also investigated. The catalyst-alkoxyborane adduct formed in step Ⅲ exhibits a B-O-B-N tetra-atomic ring. Reaction coordination calculations show that BH3 can react with 3-morpholin-4-yl-l-phenyl-l-propanone spontaneously, resulting in the need of 2 tool BH3 in the reaction.
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| 关 键 词： | 3-吗啉-4-基-1-苯基-1-丙酮 密度泛函理论 化学结构 量子化学 |
Studies on the Oxazaborolidine-catalyzed Enantioselective Reduction of 3-Morpholin-4-yl-1-phenyl-1-propanone with Density Functional Theory |
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| FAN Jian-fen,Lu Yun-xiang,Wang Qiu-Xia,WU Li-Fen,SUN Yun-Peng.Studies on the Oxazaborolidine-catalyzed Enantioselective Reduction of 3-Morpholin-4-yl-1-phenyl-1-propanone with Density Functional Theory[J].Chinese Journal of Structural Chemistry,2005,24(4):413-418. |
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| Authors: | FAN Jian-fen Lu Yun-xiang Wang Qiu-Xia WU Li-Fen SUN Yun-Peng |
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| Institution: | Department of Chemistry, Suzhou University, Suzhou 215006, China |
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| Abstract: | Density functional theory (DFT) has been applied to study the enantioselective reduction of 3-morpholin-4-yl-1-phenyl-1-propanone with borane catalyzed by (S)-4-benzyl-5,5- diphenyl-1,3,2-oxazaborolidine at the B3LYP/6-31G* level. All molecular species involved in the four reaction steps have been fully optimized and the structural parameters are provided, and the micro process of reaction was also investigated. The catalyst-alkoxyborane adduct formed in step III exhibits a B-O-B-N tetra-atomic ring. Reaction coordination calculations show that BH3 can react with 3-morpholin-4-yl-1-phenyl-1-propanone spontaneously, resulting in the need of 2 mol BH3 in the reaction. |
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| Keywords: | B3LYP/6-31G* 3-morpholin-4-yl-1-phenyl-1-propanone enantioselective reduction |
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