Syntheses of chiral cyclopropanedicaboxylic acids

Abstract

Trans-1,2-cyglopropanedicarboxylic acid and trans-3, 3-dimethyl-1, 2-cyclopropanedicarboxylic acid were prepared by reaction of (一 )dimenthyl fumarate with gem-dihalides (CH2Br2, CH3CCL2CH3)catalyzedbby coalt (0), nickel (0)complex and Zn under ultrasonic waves.The chemical and optical yield of 3 increased to 79.5% and 78% respectively .the chemical and optical yield of 5 increased to 55.3% and 47.8% respectively. Addition of bidentate ligands was useful for CH2CBr2 system , but no for CH3CCL2CH3 system .Two optical isomers of cyclopropane derivatives were seperated from HPLC by chiral colunm PTrMA.

Key words: CYCLOPROPANE P, CARBOXYLIC ACID, CHIRALITY, ULTRASONIC WAVES, ULTRASONIC APPLICATION

CLC Number:

O621

Cite this article

TAN ZHILIANG;JIN SHANGDE;XU XIAOLONG. Syntheses of chiral cyclopropanedicaboxylic acids[J]. Chin. J. Org. Chem., 1993, 13(1): 48-52.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Suyan Tao, Zixin Xiang, Junjie Bai, Xiao Wan, Xiaobing Wan. Amide Hydrolysis Reaction Using tert-Butyl Nitrite [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 550-560.
[2]	Hongqiong Zhao, Miao Yu, Dongxue Song, Qi Jia, Yingjie Liu, Yubin Ji, Ying Xu. Progress on Decarboxylation and Hydroxylation of Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 70-84.
[3]	Weina Tian, Liang Xu, Yu Wei, Pengfei Li. Synthesis of Isoquinoline-3-carboxylate Chelated B,B-Diaryl Tetracoordinated Organoboron Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1792-1798.
[4]	Yongzhou Pan, Xiujin Meng, Yingchun Wang, Muxue He. Recent Progress in Electrochemical Fixation of CO₂ to Construct Carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1416-1434.
[5]	Qian Wang, Yuqi Liu, Zongquan Wu. Synthesis and Structure Control of Chiral Helical Polymers [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4141-4146.
[6]	Guangqing Guo, Zhong Lian. Application Progress of Silyl Carboxylic Acid in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3580-3589.
[7]	Jiayi Zhao, Yicong Ge, Chuan He. Construction of Silicon-Stereogenic Center via Catalytic Asymmetric Si—H/X—H Dehydrogenative Coupling [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3352-3366.
[8]	Chaoyu Wang, Shuda Dong, Tianyang Zhu, Yuqin Liu, Zihan Wu, Ruokun Feng. Cobalt-Catalyzed Decarbonylative C(8)-Acyloxylation of 1-Naphthalamine Derivatives with α-Oxocarboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1799-1810.
[9]	Tongli Zhang, Jun Yan, Jingli He, Xuezhen Kou, Jiefeng Shen, Delong Liu, Wanbin Zhang. Synthesis of Chiral 5-Aryl-2-oxazolidinones via an Ir-BiphPHOX Catalyzed Enantioselective Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1747-1758.
[10]	Zhiliang Chu, Huijuan Chen, Shuai Shan, Xiaona Wang, Chunfang Gao, Guirong Qu, Zhongyu Liu, Haiming Guo. One-Step Synthesis of 1,2,4-Triazolo[3,4-i]purine Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1551-1556.
[11]	Yuxi Zhu, Ting Xiao, Dong Xia, Wenchao Yang. Recent Advances in the Decarboxylative Fluoroalkylation of Fluoroalkyl Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4067-4077.
[12]	Jieming Zhang, Hang Ni, Qi Wu, Junfeng Yang, Junliang Zhang. Development of P, S and Si-Stereogenic Compounds Synthesis via Palladium Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3118-3128.
[13]	Zhengjiang Fu, Xihan Cao, Jian Yin, Zhenyu Gou, Xuezheng Yi, Hu Cai. ortho-C—H Bond Functionalization of Carboxylic Acid Using Carboxyl as a Traceless Directing Group Based on the Strategy of “Two Birds with One Stone” [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 67-74.
[14]	Sha Zhou, Mukuo Wang, Weibin Xie, Shaa Zhou, Lixia Xiong, Yu Zhao, Zhengming Li. Synthesis and Insecticidal Activities of Novel Optically Active Dicarboxamides Containing N-Trifluoroacetyl Sulfulimiyl Substituents [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3532-3538.
[15]	Changming Xu, Jincheng Huang. Highly Efficient Synthesis of 1H-Indazole-3-carboxylic Acid Derivatives via Diazotization Reaction [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3256-3263.

手性环丙烷二羧的合成