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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (10): 1213-1216. 上一篇    下一篇

研究论文

(4S)-苯氧基-(S)-脯氨酸催化直接不对称羟醛缩合反应

沈宗旋, 周华, 马济美, 刘艳华, 张雅文*   

  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
  • 收稿日期:2003-12-01 修回日期:2004-02-20 接受日期:2004-04-15 发布日期:2022-09-20
  • 基金资助:
    江苏省有机合成重点实验室(No. JSK015)资助项目.

Direct Asymmetric Aldol Reactions Catalyzed by (4S)-Phenoxy-(S)-proline

SHEN Zong-Xuan, ZHOU Hua, MA Ji-Mei, LIU Yan-Hua, ZHANG Ya-Wen*   

  1. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou 215006
  • Received:2003-12-01 Revised:2004-02-20 Accepted:2004-04-15 Published:2022-09-20
  • Contact: * E-mail: zhangyw@suda.edu.cn

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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%.

关键词: 羟醛缩合反应, 催化, 不对称

The Mitsunobu reaction of N-ethoxycarbonyl-(4R)-hydroxy-(S)-proline methyl ester with phenol afforded (4S)-phenoxy-(S)-proline methyl ester, which, after saponificationand 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%.

Key words: Aldol reaction, catalysis, asymmetric