Enantioselective Desymmetrization of Phosphinic Acids via Cu-Catalyzed O-Arylation

被引:0
|
作者
Yan, Ming [1 ]
Zou, Jia-wei [2 ]
Fang, Dong-mei [1 ]
Zhang, Shi-qi [1 ]
Cui, Xin [1 ]
Tang, Zhuo [1 ]
Li, Guang-xun [1 ]
机构
[1] Chinese Acad Sci, Chengdu Inst Biol, Biol Resources Applying Ctr, Chengdu 610041, Sichuan, Peoples R China
[2] Leshan Normal Univ, Dept New Energy Mat & Chem, Leshan 614004, Sichuan, Peoples R China
来源
ACS CATALYSIS | 2025年 / 15卷 / 06期
关键词
Enantioselective desymmetrization; Copper catalysis; Chiral phosphorus compounds; Diaryliodonium salt; Phosphinic acid; EFFICIENT ASYMMETRIC-SYNTHESIS; P-STEREOGENIC PHOSPHINAMIDES; CHIRAL PHOSPHINES; P(O)-OH COMPOUNDS; OXIDES; ACCESS; LIGANDS; AMINOPHOSPHINES; CYCLIZATION; INHIBITORS;
D O I
10.1021/acscatal.5c00439
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Enantioselective desymmetrization of phosphinic acid with two completely different carbon substituents on the P atom is an efficient way to obtain chiral P(V) compounds with high structural diversity. Herein, we reported a Cu-catalyzed asymmetric arylation of phosphinic acid, which turns the P-center to be a versatile electrophile for obtaining a series of chiral P(V) compounds, including phosphinates, phosphinamides, and tertiary phosphine oxides, in good yields and high enantioselectivities.
引用
收藏
页码:4719 / 4725
页数:7
相关论文
共 50 条
  • [31] Facile access to polysubstituted Indoles via a cascade Cu-catalyzed arylation - Condensation process
    Chen, Yu
    Xie, Xiaoan
    Ma, Dawei
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24): : 9329 - 9334
  • [32] Cu-catalyzed enantioselective decarboxylative cyanation via the synergistic merger of photocatalysis and electrochemistry
    Yuan, Yin
    Yang, Junfeng
    Zhang, Junliang
    CHEMICAL SCIENCE, 2023, 14 (03) : 705 - 710
  • [33] Cu-catalyzed borylative coupling enables desymmetrization of meso-dibromocycloalkenes
    Zhan, Baoquan
    He, Chuan
    CHEM CATALYSIS, 2023, 3 (09):
  • [34] Synthesis of cyclopropene α-amino acids via enantioselective desymmetrization
    Zhang, Fan
    Fox, Joseph M.
    ORGANIC LETTERS, 2006, 8 (14) : 2965 - 2968
  • [35] Cu-catalyzed enantioselective allylic alkylation with organolithium reagents
    Valentín Hornillos
    Sureshbabu Guduguntla
    Martín Fañanás-Mastral
    Manuel Pérez
    Pieter H Bos
    Alena Rudolph
    Syuzanna R Harutyunyan
    Ben L Feringa
    Nature Protocols, 2017, 12 : 493 - 505
  • [36] Cu-catalyzed asymmetric allylic arylation with aryl lithium reagents
    Guduguntla, Sureshbabu
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [37] Cu-Catalyzed Direct C6-Arylation of Indoles
    Yang, Youqing
    Li, Ruirui
    Zhao, Yue
    Zhao, Dongbing
    Shi, Zimangzhi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (28) : 8734 - 8737
  • [38] Enantioselective synthesis of cyclobutanes via sequential Rh-catalyzed bicyclobutanation/Cu-catalyzed homoconjugate addition
    Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, United States
    J. Am. Chem. Soc., 2013, 25 (9283-9286):
  • [39] Cu-catalyzed enantioselective allylic alkylation with organolithium reagents
    Hornillos, Valentin
    Guduguntla, Sureshbabu
    Fananas-Mastral, Martin
    Perez, Manuel
    Bos, Pieter H.
    Rudolph, Alena
    Harutyunyan, Syuzanna R.
    Feringa, Ben L.
    NATURE PROTOCOLS, 2017, 12 (03) : 493 - 505
  • [40] Enantioselective Synthesis of Cyclobutanes via Sequential Rh-catalyzed Bicyclobutanation/Cu-catalyzed Homoconjugate Addition
    Panish, Robert
    Chintala, Srinivasa R.
    Boruta, David T.
    Fang, Yinzhi
    Taylor, Michael T.
    Fox, Joseph M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (25) : 9283 - 9286