| 脯氨酸催化的甲基酮与a-酮酸酯间的不对称Aldol反应 |
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| 引用本文： | 王亚军,沈宗旋,李 斌,张雅文.脯氨酸催化的甲基酮与a-酮酸酯间的不对称Aldol反应[J].中国化学,2006,24(9):1196-1199. |
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| 作者姓名： | 王亚军 沈宗旋 李 斌 张雅文 |
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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 215006, China |
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| 基金项目： | Project supported by the 0pen Program of the Key Laboratory of 0rganic Synthesis of Jiangsu Province （No. JSK 015）. Dedieated to Protessor Xikui Jiang on the occasion of his 80th birthday. |
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| 摘 要： | 以脯氨酸为催化剂，实现了甲基酮与a-酮酸酯间的不对称Aldol反应，以43%-93%的产率和最高达81％的ee得到多种a-羟基酸酯。空间效应看来是影响反应活性和选择性的一个重要因素。丙酮表现出比丁酮高的反应活性，而在某些情况下
丁酮则呈现更高的对映选择性。
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| 关 键 词： | 脯氨酸 催化作用 不对称反应 羟醛加成反应 α-酮酯 甲基酮 |
| 收稿时间： | 2005-09-21 |
| 修稿时间： | 2005-09-212006-05-10 |
Proline Catalyzed Asymmetric Aldol Reaction between Methyl Ketones and a-Ketoesters |
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| WANG Ya-Jun, SHEN Zong-Xuan, LI Bin, ZHANG Ya-Wen.Proline Catalyzed Asymmetric Aldol Reaction between Methyl Ketones and a-Ketoesters[J].Chinese Journal of Chemistry,2006,24(9):1196-1199. |
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| Authors: | WANG Ya-Jun SHEN Zong-Xuan LI Bin ZHANG Ya-Wen |
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| Institution: | Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu 215006, China |
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| Abstract: | Direct asymmetric aldol additions of acetone/and butanone to a-ketoesters were achieved using L-proline as a chiral catalyst. Various optically active a-hydroxyesters were obtained in the yields of 43%-93% with enantioselectivities up. to 81% e.e. The steric effect seems to be an important factor which influences the activity and the selectivity of the reaction. Acetone showed higher reactivity than butanone while the latter provided better enantioselectivity in some cases. |
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