Recent Advances in (Dynamic) Kinetic Resolution and Desymmetrization Catalyzed by Chiral Phosphoric Acids

被引:72
作者
Liu, Wei [1 ,2 ,3 ]
Yang, Xiaoyu [1 ]
机构
[1] ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
关键词
Asymmetric catalysis; Chiral phosphoric acids; Desymmetrization; Dynamic kinetic resolution; Kinetic resolution;
D O I
10.1002/ajoc.202100091
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Kinetic resolution, dynamic kinetic resolution and desymmetrization are practical methods to produce enantioenriched products from relatively simple racemic or achiral starting materials, which are also sometimes difficult to be accessed by other asymmetric methods. Chiral phosphoric acids, which have been recognized as one of the most powerful chiral organocatalysts to date, have also been extensively applied in the above-mentioned research fields. In this minireview, we summarized the tremendous development of kinetic resolution, dynamic kinetic resolution and desymmetrization reactions enabled by chiral phosphoric acids since the year of 2016, which were not included in the two previous outstanding reviews by Petersen et al and Dixon et al. A number of examples involving the use of CPA as cooperative catalyst are also included in this review.
引用
收藏
页码:692 / 710
页数:19
相关论文
共 50 条
  • [31] Kinetic Resolution of Diols via Etherification Catalyzed by a Chiral Phosphoric Acid: Concise Synthesis of (+)-Sacidumlignan D
    Xie, Changmin
    Bai, Donghu
    Huang, Sha-Hua
    Jia, Xueshun
    Hong, Ran
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (03) : 277 - 280
  • [32] Chiral Phosphoric Acid-Catalyzed Hydrolytic Parallel Kinetic Resolution of Racemic Epoxides and Activated Alcohols
    Du, Yi-Ying
    He, Yu-Shi
    Liang, Yan
    Liu, Xue-Song
    Liu, Juan
    Gai, Long-Hui
    Liu, Shang-Zhong
    Cao, Yi-Ming
    ORGANIC LETTERS, 2025, 27 (08) : 1786 - 1791
  • [33] Highly Enantioselective Biginelli Reaction of Aliphatic Aldehydes Catalyzed by Chiral Phosphoric Acids
    Guo, Yongbiao
    Gao, Zhenhua
    Meng, Xiangyan
    Huang, Guilan
    Zhong, Hui
    Yu, Huilan
    Ding, Xiaoqin
    Tang, Hui
    Zou, Chuanpin
    SYNLETT, 2017, 28 (15) : 2041 - 2045
  • [34] Enantioselective Robinson-Type Annulation Reaction Catalyzed by Chiral Phosphoric Acids
    Akiyama, Takahiko
    Katoh, Takuya
    Mori, Keiji
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) : 4226 - 4228
  • [35] Recent developments in organocatalytic dynamic kinetic resolution
    Pellissier, Helene
    TETRAHEDRON, 2016, 72 (23) : 3133 - 3150
  • [36] Comparative study of different chiral ligands for dynamic kinetic resolution of amino acids
    Nagaoka, Keita
    Nakano, Arina
    Han, Jianlin
    Sakamoto, Tsubasa
    Konno, Hiroyuki
    Moriwaki, Hiroki
    Abe, Hidenori
    Izawa, Kunisuke
    Soloshonok, Vadim A.
    CHIRALITY, 2021, 33 (10) : 685 - 702
  • [37] Chiral Bicyclic Imidazole-Catalyzed Acylative Dynamic Kinetic Resolution for the Synthesis of Chiral Phthalidyl Esters
    Zhou, Muxing
    Gridneva, Tatiana
    Zhang, Zhenfeng
    He, Ende
    Liu, Yangang
    Zhang, Wanbin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (03) : 1641 - 1645
  • [38] Construction of axial and point chirality through Ni-catalyzed sila-cycloaddition reaction via desymmetrization and (dynamic) kinetic resolution
    Zhu, Hua-Jie
    Shen, Ming-Hao
    Si, Jia-Wei
    Zhu, Wei-Ke
    Fang, Xiao-Jun
    Ye, Fei
    Cao, Jian
    Xu, Zheng
    Xu, Li-Wen
    SCIENCE CHINA-CHEMISTRY, 2025, : 2513 - 2523
  • [39] Recent Progress in (Dynamic) Kinetic Resolution Catalyzed by N-Heterocyclic Carbenes
    Chen, Shihao
    Shi, Yu-Hua
    Wang, Ming
    CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (17) : 2184 - 2194
  • [40] Dynamic Kinetic Resolution Approach for the Asymmetric Synthesis of Tetrahydrobenzodiazepines Using Transfer Hydrogenation by Chiral Phosphoric Acid
    Horiguchi, Kosaku
    Yamamoto, Eri
    Saito, Kodai
    Yamanaka, Masahiro
    Akiyama, Takahiko
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (24) : 8078 - 8083