(4S)-苯氧基-(S)-脯氨酸催化直接不对称羟醛缩合反应 |
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引用本文: | 沈宗旋,周华,马济美,刘艳华,张雅文.(4S)-苯氧基-(S)-脯氨酸催化直接不对称羟醛缩合反应[J].有机化学,2004,24(10):1213-1216. |
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作者姓名: | 沈宗旋 周华 马济美 刘艳华 张雅文 |
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作者单位: | 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 |
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摘 要: | N-乙氧羰基-(4R)-羟基-(S)-脯氨酸甲酯与苯酚的Mitsunobu反应给出N-乙氧羰基-(4S)-苯氧基-(S)-脯氨酸甲酯,后者经皂化和盐酸水解后得标题氨基酸.这一化合物(5 mol%)对映选择性催化丙酮和取代苯甲醛的羟醛缩合反应,产率67.4%~89.9%,ee最高达76.5%.
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关 键 词: | 羟醛缩合反应 催化 不对称 |
修稿时间: | 2003年12月1日 |
Direct Asymmetric Aldol Reactions Catalyzed by (4S)-Phenoxy-( S )-proline |
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Abstract: | The Mitsunobu reaction of N-ethoxycarbonyl-(4R)-hydroxy-(S)-proline methyl ester with phenol afforded (4S)-phenoxy-(S)-proline methyl ester, which, after saponification and hydrolysis in hydrochloric acid, gave the title amino acid. This compound (5 mol%) catalyzes aldol reaction of acetone with benzaldehydes enantioselectively in the yields ranging from 67.4% to 89.9%, with the ee up to 76.5%. |
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Keywords: | Aldol reaction catalysis asymmetric |
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