Study on the Highly Diastereoselective Synthesis and Structure of trans-2,3-Diaryl Substituted 1-Aminocyclopropanecarboxylic Acid Derivatives

Acta Chimica Sinica ›› 2004, Vol. 62 ›› Issue (19): 1941-1947. Previous Articles Next Articles

反式2,3-二芳基取代-1-氨基环丙烷羧酸的合成及其结构研究

苏桂发^1,2, 潘成学¹, 牟红涛¹, 曾陇梅², 郁开北³

1. 广西师范大学化学化工学院, 桂林, 541004;
2. 中山大学化学院, 广州, 510275;
3. 中国科学院成都有机化学研究所, 成都, 610041

投稿日期:2003-12-30 修回日期:2004-05-15 发布日期:2014-02-17
通讯作者: 苏桂发,E-mail:su_gf@sina.com E-mail:su_gf@sina.com
基金资助:
广西自然科学基金(No.0339033)、广西高校百名中青年学科带头人资助计划资助项目.

Study on the Highly Diastereoselective Synthesis and Structure of trans-2,3-Diaryl Substituted 1-Aminocyclopropanecarboxylic Acid Derivatives

SU Gui-Fa^1,2, PAN Cheng-Xue¹, MU Hong-Tao¹, ZENG Long-Mei², YU Kai-Bei³

1. College of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin 541004;
2. College of Chemistry and Chemical Engineering, Zhongshan University, Guangzhou 510275;
3. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041

Received:2003-12-30 Revised:2004-05-15 Published:2014-02-17

Abstract

(Z)-2-Phenyl-4-arylidene-4,5-dihydro-oxazol-5-ones were synthesized by condensation of hippuric acid and aromatic aldehyde following the Erlenmeyer procedure, then reacted with aryldiazomethane in a highly diastereoselective 1,3-dipolar cycloaddition at room temperature to give spirocyclopropane derivatives in 86%～90% yields. The spirocyclopropane derivatives were readily converted into the corresponding trans- 2,3-diaryl-1-aminocyclopropanecarboxylic acid by treatment with absolute methanol containing catalytic amounts of sodium methoxide, then hydrolysis in 4 mol/L of HCl/HOAc. The structures and configurations were established on the basis of their elemental analyses and spectroscopic data, such as IR, ¹H NMR, ¹³C NMR, MS and X-ray crystallography. The results indicated that 2,3-diaryl-1-aminocyclopropanecarboxylic acids with desired configurations could be synthesized with certain aromatic aldehyde and appropriate aryldiazomethane.

Key words: trans-2,3-diaryl substituted-1-aminocyclopropanecarboxylic acid, highly diastereoselective synthesis, 1,3-dipolar cycloaddition, X-ray crystallography

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SU Gui-Fa, PAN Cheng-Xue, MU Hong-Tao, ZENG Long-Mei, YU Kai-Bei. Study on the Highly Diastereoselective Synthesis and Structure of trans-2,3-Diaryl Substituted 1-Aminocyclopropanecarboxylic Acid Derivatives[J]. Acta Chimica Sinica, 2004, 62(19): 1941-1947.

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反式2,3-二芳基取代-1-氨基环丙烷羧酸的合成及其结构研究

Study on the Highly Diastereoselective Synthesis and Structure of trans-2,3-Diaryl Substituted 1-Aminocyclopropanecarboxylic Acid Derivatives

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