Kinetic Resolution of β-Hydroxy Epoxides Promoted by ChiralAluminium Reagents

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Chin. J. Org. Chem. ›› 2005, Vol. 25 ›› Issue (10): 1302-1305. Previous Articles Next Articles

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手性铝试剂促进的β-环氧醇动力学拆分研究

王少华，王飞，张辅民
樊春安，涂永强*，任世阔

(兰州大学化学化工学院功能有机分子化学国家重点实验室兰州 730000)

收稿日期:2004-12-16 修回日期:2005-04-26 发布日期:2005-10-08
通讯作者: 涂永强

Kinetic Resolution of β-Hydroxy Epoxides Promoted by ChiralAluminium Reagents

WANG Shao-Hua,WANG Fei,ZHANG Fu-Min
FAN Chun-An,TU Yong-Qiang*,REN Shi-Kuo

(State Key Laboratory of Applied Organic Chemistry, Department of Chemistry,
Lanzhou Univer-sity, Lanzhou 730000)

Received:2004-12-16 Revised:2005-04-26 Published:2005-10-08

Contact: TU Yong-Qiang

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Abstract

The first kinetic resolution of β-hydroxy epoxides has been studied through chiral aluminium reagents, which gave the recovered starting material with 60% ee. Various conditions were explored for the kinetic resolution of β-hydroxy epoxide by chiral aluminium reagents. A possible mechanism was proposed for the reaction by aluminium reagent.

Key words: kinetic resolution, β-hydroxy epoxide, chiral BINOL, triethylaluminium

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WANG Shao-Hua,WANG Fei,ZHANG Fu-Min
FAN Chun-An,TU Yong-Qiang*,REN Shi-Kuo. Kinetic Resolution of β-Hydroxy Epoxides Promoted by ChiralAluminium Reagents[J]. Chin. J. Org. Chem., 2005, 25(10): 1302-1305.

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[1]	Shuang Yang, Xinqiang Fang. Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 448-480.
[2]	Huijuan Hu, Qiaoli Yan, Xiaogang Lu, Qifan Yang, Chengxin Pei, Hongmei Wang, Runli Gao. Kinetic Resolution of Racemic P-Chiral α-Hydroxymethylphos-phonates Catalyzed by Lipase from Porcine Pancreas [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2815-2825.
[3]	Yangyang Chu, Zhaobin Han, Kuiling Ding. Progresses in the Application of Kinetic Resolution in Transition Metal Catalyzed Asymmetric (Transfer) Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1934-1951.
[4]	Cheng Luo, Yanli Yin, Zhiyong Jiang. Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1963-1976.
[5]	Yuliang Chen, Fengkai He, Siyun Wang, Dingcheng Jia, Yaqun Liu, Yiyong Huang. Kinetic Resolution of Aldehydes Bearing an All-Carbon Quaternary Stereocenter at the α-Position by the Antilla Allylboration [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4294-4302.
[6]	Yunrong Chen, Wei Liu, Xiaoyu Yang. Recent Advances in Kinetic Resolution of Tertiary Alcohols [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 679-697.
[7]	Lingjie Fan, Tao Zhou, Xu Yang, Mengxue Jiang, Xinquan Hu, Bingfeng Shi. Pd(II)-Catalyzed Enantioselective C—H Olefination of 2-(Arylsulfinyl)pyridines through Kinetic Resolution [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3405-3418.
[8]	Huachao Liu, Chong Shen, Xin Chang, Chunjiang Wang. Recent Advances in Catalytic Asymmetric 1,3-Dipolar Cycloaddition Reactions with Kinetic Resolution [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3322-3334.
[9]	Hui Li, Liang Yin. Research Progress on Catalytic Asymmetric Synthesis of P-Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3183-3200.
[10]	Tang Liang, Li Xuewei, Xie Fang, Zhang Wanbin. Catalytic Kinetic Resolution of Amines and Their Derivatives by Non-acylation Reaction [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 575-588.
[11]	Zhang Qiying, Zhang Yiming, Hao Erjun, Bai Juan, Qu Guirong, Guo Haiming. Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution for the Construction of Carbocyclic N³-Purine Nucleosides [J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 376-383.
[12]	Wang Cai, Zhou Feng, Zhou Jian. Recent Advances in the Enantioselective Copper(I)-Catalyzed Azide-Alkyne Cycloaddition Reaction [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3065-3077.
[13]	Ni Guowei, Tang Jiawei, Zou Jie, Chen Shaoxin, Ju Dianwen, Zhang Fuli. Recent Advances on Carbonyl Reductases for Dynamic Kinetic Resolution [J]. Chin. J. Org. Chem., 2019, 39(2): 339-349.
[14]	Deng Dun, Zhang Yun, Sun Aijun, Sai Ke, Hu Yunfeng. Functional Characterization of a New Antarctic Microbial Esterase EST112-2 and Its Use in the Preparation of Chiral Tertiary Alcohol (S)-Linalool [J]. Chin. J. Org. Chem., 2018, 38(5): 1185-1192.
[15]	Yang Jinchuang, Li Guosong, Lü Chengwei, An Yue, Gao Shuang. Oxidation Kinetics Resolution of Racemic Aromatic Sulfoxides by Chiral Porphyrin-Inspired N4 Ligand with Manganese Complex [J]. Chin. J. Org. Chem., 2018, 38(11): 3070-3077.