Effect of Chelate Size of Bisoxazolines on the Enantioselectivity of the Asymmetric Aziridination

Abstract

Chiral bisoxazolines have been widely applied ligands to asymmetric catalysis and a series of optically active bisoxazolines with rigid backbones and different chelate sizes were synthesized. The effect of their chelate sizes on the enantioselectivity was investigated in the asymmetric aziridination. The results indicate that tuning chelate size can not only change the enantioselectivity, but also change the enantiofacial se-lectivity completely.

Key words: chelate size, asymmetric aziridination, ligand, enantioselectivity, bisoxazoline

Cite this article

MA Lin-Ge,DU Da-Ming,XU Jia-Xi*. Effect of Chelate Size of Bisoxazolines on the Enantioselectivity of the Asymmetric Aziridination[J]. Chin. J. Org. Chem., 2006, 26(04): 568-572.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Hao Qin, Chuanjin Hou, Dinghua Liang, Xinwei He, Ling Li, Xiangping Hu. Chiral P,N,N-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 282-290.
[2]	Wenfang Wang. Recent Progress in Transition-Metal-Catalyzed Asymmetric C—H Borylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3146-3166.
[3]	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.
[4]	Yannian Pan, Xiao Qin, Chengkai Yuan, Yi Lu. Application of Ligands in Cp*Rh(III)-Catalyzed C—H Bond Functionalization Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 924-948.
[5]	Tingting Liu, Yucai Hu, An Shen. Mechanism of Carbon-Carbon Coupling Reactions Catalyzed by Imine-Ligand-Assisted N-Heterocyclic Carbene Palladium Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 622-628.
[6]	Xuqin Zhong, Zhen Liu. Conformational Screening of the Catalyst System Containing Transition Metal and Flexible Ligand [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 734-741.
[7]	Licheng Wu, Xianqing Wu, Jingping Qu, Yifeng Chen. Exploration of Quinim Ligand in Ni-Catalyzed Enantioselective Reductive Carbamoyl-Alkylation of Alkene [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4239-4250.
[8]	Zehui Li, Haoyu Zou, Lincai Li, Yiling Zhao, Hongping Zhu. Synthesis and Propylene Oxide Carbonylation Hydroesterification Catalytic Property of N,O-Ligand Coordination Cobalt Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3907-3915.
[9]	Wei Xiong, Bin Shi, Xuan Jiang, Liangqiu Lu, Wenjing Xiao. Ligand-Switched Pd-Catalyzed Divergent Transformations of Vinyl Cyclic Carbamates and Isocyanates [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 265-273.
[10]	Li Dai, Di Xu, Yifei Mao, Jiaqi Zhu, Mengjiao Yang. Structures and Synthetic Strategies of Chiral Oxazolinyl Ferrocene Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2364-2375.
[11]	Tao Li, Yi Liu, Xue Bai, Zunjun Zhou, Peng Zuo, Miaofeng Ma, Chong-Min Zhong, Ya-Jie Zuo. Preparation of Imidazolium Ion Functionalized HG-II Chiral Ruthenium Catalysts and Their Catalytic Performance in Asymmetric Olefin Metathesis [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1713-1721.
[12]	Jiahao Li, Hongqiang Liu, Bo Zhang, Bingyang Ge, Dawei Wang. Synthesis of Supported Indazolyl-Pyridyl-Quinoline Iridium Catalyst and Its Application to N-Alkylation of 2-Aminobenzothiazoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 619-630.
[13]	Hui Yan, Man Zhang, Lin Li, Teng Hu, Wulin Yang. Advances in the Catalytic Asymmetric Synthesis of Chiral Spiroketals [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3640-3657.
[14]	Yuanyuan Ping, Haixia Song, Wangqing Kong. Recent Advances in Ni-Catalyzed Asymmetric Reductive Difunctionalization of Alkenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3302-3321.
[15]	Shihu Jia, Siyuan Chen, Zeshui Liu, Honggang Cheng, Qianghui Zhou. Pd/Novel Axially Chiral Phosphine-Alkene Ligands Catalyzed Asymmetric Allylic Alkylation of Indoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3373-3381.

在不对称氮杂环丙烷化中双噁唑啉配位空间大小对对映选择性的影响