高等学校化学学报

高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (8): 1256.

• 论文 • 上一篇    下一篇

利用手性N-氰乙基-2-羟基蒎烷-3-酮亚胺合成光学活性2-乙基环丙烷氨基酸

苏桂发1, Philippe Dorizon2, Jean Ollivier2, Jacques Salaün2   

  1. 1. 广西师范大学化学化工系, 桂林, 541004;
    2. 南巴黎大学碳环实验室, 91405, OrsayCédéx, 法国
  • 收稿日期:1997-06-07 出版日期:1998-08-24 发布日期:1998-08-24
  • 通讯作者: 苏桂发,男,34岁,副教授.
  • 作者简介:苏桂发,男,34岁,副教授.
  • 基金资助:

    广西省教育委员会科研基金资助课题.

Asymmetric Synthesis of Optically Active 2-Ethyl-1-Amino-cyclopropanecarboxylic Acid via Pianone Ketimine

SU Gui-Fa1, Philippe Dorizon2, Jean Ollivier2, Jacques Salaün2   

  1. 1. Department of Chemistry & Chemical Engineering, Guangxi Normal University, Guilin, 541004;
    2. Laboratoire des Carbocycles, ICMO, Bat 420, Universitéde Paris-Sud, 91405, Orsay Cédéx, France
  • Received:1997-06-07 Online:1998-08-24 Published:1998-08-24

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被引次数

7

摘要： 以2-羟基蒎烷-3-酮(1)与氨基乙腈缩合得到的手性酮亚胺(2)为中间体,经去质子化,在Pd(0)催化下与1,4-二氯-2-丁烯(3)发生串联反应,得到光学活性环丙烷衍生物(4),产率约为70%,反应的非对映立体选择性(d.e.)为100%.化合物4经选择性还原后水解,即可制得光学活性2-乙基环丙烷氨基酸,产物的对映体过量(e.e.)为33%.

关键词: 2－羟基蒎烷－3－酮, 1, 4－二氯－2－丁烯, 手性亚胺, 串联反应, 2－乙基环丙烷氨基酸

Abstract: Optically active cyclopropanes(4) were obtained by using 2-hydroxypinan-3-one 1 as a chiral auxiliary, condensed with aminoacetonitrile to form a chiral ketimine 2 followed by Pd(0) catalyzed tandem alkylation and SN'cyclisation of 1,4-dichlorobut-2-ene 3 with chiral ketimine 2. The yields are 69% and the diastereoselectivities of reaction are 100%. After the selective reduction of ethenyl group of 4, then by simple acid hydrolysis, optically active-2-ethyl 1-amino-cyclopropanecarboxylic acid 6 could be obtained, the e.e. value of 6 is 33%.

Key words: 2-Hydroxypinan-3-one, 1,4-Dichlorobut-2-ene, Chiral imine, Tandem reaction, 2-Ethyl-1-mino-cyclopropanecarboxylic acid

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