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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (6): 621-625. 上一篇    下一篇

研究论文

手性双氨基醇-Et2Zn催化的不对称直接羟醛缩合反应

沈宗旋a, 王建非a, 俞学炜b, 刘艳华a, 韩玉峰a, 张雅文*,a   

  1. a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
    b江苏省苏州卫生学校 苏州 215007
  • 收稿日期:2003-08-19 修回日期:2003-11-04 接受日期:2003-12-15 发布日期:2022-09-21
  • 通讯作者: *E-mail: zhangyw@suda.edu.cn
  • 基金资助:
    江苏省教育厅自然科学基金(No. 01KJB150002)资助项目.

Chiral Bisaminoalcohol-Et2Zn-Catalyzed Asymmetric Direct Aldol Reactions

SHEN, Zong-Xuana, WANG, Jian-Feia, YU, Xue-Weib, LIU, Yan-Huaa, HAN, Yu-Fenga, ZHANG, Ya-Wen*,a   

  1. a The Key Laboratory of Organic Synthesis of Jiangsu Province, College ofChemistry and Chemical Engineering, Suzhou University, Suzhou 215006
    b Suzhou Health School, Jiangsu, Suzhou 215007
  • Received:2003-08-19 Revised:2003-11-04 Accepted:2003-12-15 Published:2022-09-21

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以1,3-二溴丙酮和(2′S)-(二苯基羟甲基)-四氢吡咯为原料,合成了两种新型手性氨基醇1,3-双[(2′S)-(二苯基羟甲基)-1-四氢吡咯基]丙酮(3)和1,3-双[(2′S)-(二苯基羟甲基)-1-四氢吡咯基]-2-丙醇(4),总产率分别为39%和35%.手性双氨基醇3-/4-Et2Zn可催化未修饰醛、酮的不对称直接羟醛缩合反应,对映体过量最高9%.

关键词: 手性氨基醇, 不对称直接羟醛缩合反应, 催化剂

Two novel chrial bisaminoalcohols,1,3-bis-[(2′S)-(diphenylhydroxymethyl)pyrrolidin-1-yl]-2-pro~pa~none (3) and 1,3-bis-[(2′S)-(diphenylhydroxymethyl)pyrrolidin-1-yl]-2-propanol (4), were prepared using the 1,3-dibromo-2-propanone and (2′S)-(diphenylhydroxymethyl)pyrrolidine as the starting materials. The yields were 39% and 35%, respectively. The asymmetricdirect aldol reactions of unmodified ketones and aldehydes were achieved with the ee up to 9% by using the bisaminoalcohol-diethylzinc as the catalyst.

Key words: chiral β-aminoalcohol, direct aldol reaction, catalyst