| 环磺酰胺手性辅助试剂诱导不对称羟醛缩合反应的研究 |
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| 引用本文： | 胡蕾,卢桃桃,王小兰,张吉书,卢翠芬,杨桂春,陈祖兴. 环磺酰胺手性辅助试剂诱导不对称羟醛缩合反应的研究[J]. 湖北大学学报(自然科学版), 2013, 0(1): 98-103 |
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| 作者姓名： | 胡蕾 卢桃桃 王小兰 张吉书 卢翠芬 杨桂春 陈祖兴 |
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| 作者单位： | 湖北大学化学化工学院;湖北省黄冈中学 |
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| 基金项目： | 国家自然科学基金(21042005)资助 |
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| 摘 要： | 以L-苯丙氨基醇为原料合成一种新颖的3-苄基-5-正丁基环磺酰胺手性辅助试剂，将其酰化后应用于不对称羟醛缩合反应，具有很高的化学产率（85％～94％）和syn式非对映选择性（dr：92：8～99：1）．羟醛缩合产物5a解脱后高产率得到近乎光学纯的产物（2S，3S）-3-羟基-2-甲基-3-苯基丙酸6a，同时可定量回收环磺酰胺手性辅助试剂．
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| 关 键 词： | 环磺酰胺 手性辅助试剂 诱导 羟醛缩合 |
Asymmetric aldol reactions using a chiral cyclosulfamide as the chiral auxiliary |
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| HU Lei,LU Taotao,WANG Xiaolan,ZHANG Jishu,LU Cuifen,YANG Guichun,CHEN Zuxing. Asymmetric aldol reactions using a chiral cyclosulfamide as the chiral auxiliary[J]. Journal of Hubei University(Natural Science Edition), 2013, 0(1): 98-103 |
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| Authors: | HU Lei LU Taotao WANG Xiaolan ZHANG Jishu LU Cuifen YANG Guichun CHEN Zuxing |
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| Affiliation: | 1(1.School of Chemistry and Chemical Engineering,Hubei University,Wuhan 430062,China; 2.Huanggang Middle School in Hubei Province,Huangzhou 438000,China) |
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| Abstract: | A novel cyclosulfamiade chiral auxiliary was prepared starting from L phenylpropanotamine, which was used to induce asymmetric aldol reactions after acylation. The aldol reactions induced by chiral cyclosulfamiade occurred in good yields （85%- 94%） with high syn diastereoselectivities （dr： 92 ： 8-99 ： 1）. Aldol adduct 5a was readily cleaved by hydrolysis to afford almost enantiomerically pure （2S, 3S）-3-hydroxy-2-methyl-3-phenyl propionic acid 6a in good yield. The chiral auxiliary could be recovered quantitatively in this process. |
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| Keywords: | cyclosulfamiade chiral auxiliary induce aldol |
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