Chiral phosphoric acid catalyzed asymmetric addition of naphthols to para-quinone methides

被引：92
|
作者：
Wong, Yuk Fai [1 ]
Wang, Zhaobin [1 ]
Sun, Jianwei [1 ]
机构：
[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 24期
关键词：
BRONSTED ACID; 1,6-CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; ACTIVATION; TRIARYLMETHANES; BIOSYNTHESIS; ALKYLATION; POLYMERS; STYRENES; ALCOHOLS;
D O I：
10.1039/c6ob00125d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An asymmetric addition of naphthols to in situ generated para-quinone methides catalyzed by a chiral phosphoric acid is described. A range of useful triarylmethanes can be generated from stable general para-hydroxybenzyl alcohols with good efficiency and enantioselectivity.
引用
收藏
页码：5751 / 5754
页数：4
相关论文
共 50 条
  • [1] Phosphoric Acid Catalyzed Asymmetric 1,6-Conjugate Addition of Thioacetic Acid to para-Quinone Methides
    Dong, Nan
    Zhang, Zhi-Pei
    Xue, Xiao-Song
    Li, Xin
    Cheng, Jin-Pei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (04) : 1460 - 1464
  • [2] Asymmetric Synthesis of Dihydrocoumarins through Chiral Phosphoric Acid-Catalyzed Cycloannulation of para-Quinone Methides and Azlactones
    Zhang, Zhi-Pei
    Xie, Kai-Xue
    Yang, Chen
    Li, Man
    Li, Xin
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01): : 364 - 373
  • [3] Asymmetric Cycloaddition of ortho-Hydroxyphenyl-Substituted para-Quinone Methides and Enamides Catalyzed by Chiral Phosphoric Acid
    Yang, Guo-Hui
    Zhao, Qun
    Zhang, Zhi-Pei
    Zheng, Han-Liang
    Chen, Li
    Li, Xin
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12): : 7883 - 7893
  • [4] Primary activation of para-quinone methides by chiral phosphoric acid for enantioselective construction of tetraarylmethanes
    Han, Zhengyu
    Zhu, Biao
    Zang, Yu
    Zhang, Chaoshen
    Dong, Xiu-Qin
    Huang, Hai
    Sun, Jianwei
    CHEMICAL SCIENCE, 2024, 15 (02) : 720 - 725
  • [5] Chiral Br?nsted acid-catalyzed asymmetric intermolecular [4 + 2] annulation of ynamides with para-quinone methides
    HangHao Li
    YaNan Meng
    CanMing Chen
    YuQi Wang
    ZhiXin Zhang
    Zhou Xu
    Bo Zhou
    LongWu Ye
    Science China(Chemistry), 2023, 66 (05) : 1467 - 1473
  • [6] Chiral Bronsted acid-catalyzed asymmetric intermolecular [4+2] annulation of ynamides with para-quinone methides
    Li, Hang-Hao
    Meng, Ya-Nan
    Chen, Can-Ming
    Wang, Yu-Qi
    Zhang, Zhi-Xin
    Xu, Zhou
    Zhou, Bo
    Ye, Long-Wu
    SCIENCE CHINA-CHEMISTRY, 2023, 66 (05) : 1467 - 1473
  • [7] Chiral Br?nsted acid-catalyzed asymmetric intermolecular [4 + 2] annulation of ynamides with para-quinone methides
    Hang-Hao Li
    Ya-Nan Meng
    Can-Ming Chen
    Yu-Qi Wang
    Zhi-Xin Zhang
    Zhou Xu
    Bo Zhou
    Long-Wu Ye
    Science China(Chemistry), 2023, (05) : 1467 - 1473
  • [8] Chiral Brønsted acid-catalyzed asymmetric intermolecular [4 + 2] annulation of ynamides with para-quinone methides
    Hang-Hao Li
    Ya-Nan Meng
    Can-Ming Chen
    Yu-Qi Wang
    Zhi-Xin Zhang
    Zhou Xu
    Bo Zhou
    Long-Wu Ye
    Science China Chemistry, 2023, 66 : 1467 - 1473
  • [9] Acetic Acid-Catalyzed 1,6-Addition of Indolizine to para-Quinone Methides
    Lafzi, Ferruh
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (07)
  • [10] Asymmetric Boration of para-Quinone Methides Catalyzed by N-Heterocyclic Carbene
    Wu Yuzhu
    Shen Panpan
    Duan Wenzeng
    Ma Yudao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (05) : 1483 - 1492
12345