| DFT Study on the Origin of the Enantioselectivity of （S）-4-Hydroxylproline-Catalyzed Direct Aldol Reaction between Acetone and 4-Nitrobenzaldehyde |
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| 引用本文： | 樊建芬,吴丽芬,孙云鹏.DFT Study on the Origin of the Enantioselectivity of （S）-4-Hydroxylproline-Catalyzed Direct Aldol Reaction between Acetone and 4-Nitrobenzaldehyde[J].中国化学,2007,25(4):472-477. |
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| 作者姓名： | 樊建芬 吴丽芬 孙云鹏 |
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| 作者单位： | Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu 215123, China |
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| 基金项目： | Project supported by the Research Foundation of Key Laboratory of 0rganic Synthesis of Jiangsu Province （No. JSK010）. |
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| 摘 要： | DFT-B3LYP calculations were carried out to study the enantioselectivity of the （S）-4-hydroxylproline-catalyzed direct aldol reaction between acetone and 4-nitrobenzaldehyde. Four transition structures associated with the stereo-controlling step of the reaction have been determined. They are corresponding to the anti and syn arrangements of the methylene moiety related to the carboxylic acid group in enamine intermediate and the si and re attacks to the aldehyde carbonyl carbon. The effect of DMSO solvent on the stereo-controlling step was investigated with polarized continuum model （PCM）. The computed energies of the transition states reveal the moderate enantioselectivity of the reaction.
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| 关 键 词： | (S)-4-羟基脯氨酸 催化 丙酮 4-硝基苯甲醛 直接羟醛缩合反应 对映选择性 DFT |
| 修稿时间： | 2006-04-262006-12-13 |
DFT Study on the Origin of the Enantioselectivity of （S）-4-Hydroxylproline-Catalyzed Direct Aldol Reaction between Acetone and 4-Nitrobenzaldehyde |
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| FAN Jian-Fen, WU Li-Fen, SUN Yun-Peng.DFT Study on the Origin of the Enantioselectivity of （S）-4-Hydroxylproline-Catalyzed Direct Aldol Reaction between Acetone and 4-Nitrobenzaldehyde[J].Chinese Journal of Chemistry,2007,25(4):472-477. |
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| Authors: | FAN Jian-Fen WU Li-Fen SUN Yun-Peng |
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| Institution: | Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu 215123, China |
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| Abstract: | DFT‐B3LYP calculations were carried out to study the enantioselectivity of the (S)‐4‐hydroxylproline‐catalyzed direct aldol reaction between acetone and 4‐nitrobenzaldehyde. Four transition structures associated with the stereo‐controlling step of the reaction have been determined. They are corresponding to the anti and syn arrangements of the methylene moiety related to the carboxylic acid group in enamine intermediate and the si and re attacks to the aldehyde carbonyl carbon. The effect of DMSO solvent on the stereo‐controlling step was investigated with polarized continuum model (PCM). The computed energies of the transition states reveal the moderate enantioselectivity of the reaction. |
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| Keywords: | B3LYP enantioselectivity （S）-4-hydroxylproline direct aldol reaction acetone 4-nitrobenzaldehyde |
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