| N-[(S)-脯氨酰]羟胺的合成及催化直接不对称羟醛反应研究 |
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| 引用本文： | 丁一,张雅文,刘艳华,罗晓清,马济美,沈宗旋. N-[(S)-脯氨酰]羟胺的合成及催化直接不对称羟醛反应研究[J]. 有机化学, 2005, 25(5): 567-569 |
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| 作者姓名： | 丁一 张雅文 刘艳华 罗晓清 马济美 沈宗旋 |
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| 作者单位： | 1. 苏州大学化学化工学院江苏省有机合成重点实验室,苏州,215006
2. 苏州卫生学校,苏州,215007 |
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| 摘 要： | (S)-脯氨酸用苯甲氧羰酰氯保护氨基后用混合酸酐法与羟胺偶合, 给出N-[N-苯甲氧羰酰-(S)-脯氨酰]羟胺, 催化氢解脱去保护基得标题化合物. 该化合物对映选择性催化直接羟醛反应, 产率最高达到90.0%, 对映体过量最高达89.5%.
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| 关 键 词： | 直接不对称羟醛反应 手性催化剂 (S)-脯氨酰羟胺 |
| 收稿时间： | 2004-09-13 |
| 修稿时间： | 2004-12-06 |
Synthesis of N-(S)-Prolylhydroxylamine and Its Cataly-sis in Direct Asymmetric Aldol Reactions |
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| DING Yi,ZHANG Ya-Wen,LIU Yan-Hua,LUO Xiao-Qing,MA Ji-Mei,SHEN Zong-Xuan. Synthesis of N-(S)-Prolylhydroxylamine and Its Cataly-sis in Direct Asymmetric Aldol Reactions[J]. Chinese Journal of Organic Chemistry, 2005, 25(5): 567-569 |
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| Authors: | DING Yi ZHANG Ya-Wen LIU Yan-Hua LUO Xiao-Qing MA Ji-Mei SHEN Zong-Xuan |
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| Affiliation: | (Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou 215006)(Suzhou Health School, Suzhou 215007) |
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| Abstract: | S)-Proline was N-protected using phenylmethoxycarbonyl chloride and then coupled with hydroxylamine by the method of mixed anhydride, giving N-[N-phenylmethoxycarbonyl-(S)-prolyl]- hydroxylamine, which, after deprotection by catalytic hydrogenolysis, afforded the title compound. This compound efficiently catalyzed the direct asymmetric aldol reaction with the yield up to 90.0% and enanti- omeric excess up to 89.5%. |
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| Keywords: | direct asymmetric aldol reaction chiral catalyst N-(S)-prolylhydroxylamine |
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