Asymmetric Synthesis of 2-Azabicyclo[3.1.0]hexane-3- carboxylic Acid

doi:10.6023/cjoc201403004

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (8): 1616-1622.DOI: 10.6023/cjoc201403004 Previous Articles Next Articles

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2-氮杂双环[3.1.0]己烷-3-羧酸的不对称合成

付行花, 樊俭俭, 邹爱宗, 俞娟, 何广科, 朱红军

南京工业大学理学院南京 211816

收稿日期:2014-03-03 修回日期:2014-03-31 发布日期:2014-04-18
通讯作者: 朱红军 E-mail:zhuhj@njtech.edu.cn
基金资助:
国家“十二五科技支撑计划”（No.2011BAE06A07-04）资助项目.

Asymmetric Synthesis of 2-Azabicyclo[3.1.0]hexane-3- carboxylic Acid

Fu Xinghua, Fan Jianjian, Zou Aizong, Yu Juan, He Guangke, Zhu Hongjun

College of Sciences, Nanjing Tech University, Nanjing 211816

Received:2014-03-03 Revised:2014-03-31 Published:2014-04-18
Supported by:
Project supported by the National Key Technology R&D Program of the Ministry of Science and Technology (No. 2011BAE06A07-04).

2-Azabicyclo[3.1.0]hexane-3-carboxylic acids were obtained via amino protection, 4-dimethylaminopyridine (DMAP) catalytic cyclization, reduction-dehydration into alkene, asymmetric Simmons-Smith reaction and hydrolysis reaction from glutamic acid. The intermediates and target products were characterized by ¹H NMR and ¹³C NMR. (1R,3S,5R)- 2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid and (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo-[3.1.0]hexane-3-carboxylic acid were analyzed by X-ray diffraction as well. The process conditions about DMAP catalytic cyclization reaction, Simmons-Smith reaction and hydrolyzation were discussed. The results show that the yield of (R)-1,2-di-tert-butyl 5-oxopyrrolidine- 1,2-dicarboxyate was 82% at the ratio of n(DMAP):n(di-tert-butyl dicarbonate):n(pyridine)=0.40:4.0:1.0. The ratio of cis/trans-form varied with the reaction time in Simmons-Smith reaction, which gave a best ratio of 6:1 at 19.5 h. The total yield is 30%, and the de value is 72%.

Key words: 2-azabicyclo[3.1.0]hexane-3-carboxylic acid, glutamic acid, DMAP catalytic cyclization, hydrolysis reaction, asymmetric synthesis

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Fu Xinghua, Fan Jianjian, Zou Aizong, Yu Juan, He Guangke, Zhu Hongjun. Asymmetric Synthesis of 2-Azabicyclo[3.1.0]hexane-3- carboxylic Acid[J]. Chin. J. Org. Chem., 2014, 34(8): 1616-1622.

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2-氮杂双环[3.1.0]己烷-3-羧酸的不对称合成

Asymmetric Synthesis of 2-Azabicyclo[3.1.0]hexane-3- carboxylic Acid

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