Catalytic Asymmetric 1,6-Conjugate Addition of para-Quinone Methides: Formation of All-Carbon Quaternary Stereocenters

被引:205
|
作者
Wang, Zhaobin [1 ]
Wong, Yuk Fai [1 ]
Sun, Jianwei [1 ]
机构
[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
关键词
asymmetric catalysis; heterocycles; nucleophilic addition; organocatalysis; synthetic methods; CONJUGATE ADDITION; TRIARYLMETHANES; BIOSYNTHESIS; ALKYLATION; ALKALOIDS; POLYMERS; INDOLES; ACCESS;
D O I
10.1002/anie.201506701
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Described herein is a general and mild catalytic asymmetric 1,6-conjugate addition of para-quinone methides (p-QMs), a class of challenging reactions with previous limited success. Benefiting from chiral BrOnsted acid catalysis, which allows insitu formation of p-QMs, our reaction expands the scope to general p-QMs with various substitution patterns. It also enables efficient intermolecular formation of all-carbon quaternary stereocenters with high enantioselectivity.
引用
收藏
页码:13711 / 13714
页数:4
相关论文
共 50 条
  • [1] Organocatalyzed Asymmetric 1,6-Conjugate Addition of para-Quinone Methides with Dicyanoolefins
    Li, Xuanyi
    Xu, Xiuyan
    Wei, Weiwei
    Lin, Aijun
    Yao, Hequan
    ORGANIC LETTERS, 2016, 18 (03) : 428 - 431
  • [2] Catalytic asymmetric 1,6-conjugate addition of in situ generated para-quinone methides with tritylthiol
    Fan, Ya-Jing
    Zhou, Lei
    Li, Shen
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (11): : 1820 - 1824
  • [3] Thiourea catalyzed 1,6-conjugate addition of indoles to para-quinone methides
    Wu, Guangmiao
    Li, Tao
    Liu, Fuhai
    Zhao, Yulong
    Ma, Shiqiang
    Tang, Shouchu
    Xie, Xingang
    She, Xuegong
    TETRAHEDRON LETTERS, 2021, 81
  • [4] 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
  • [5] Mn-Catalyzed 1,6-conjugate addition/aromatization of para-quinone methides
    Yang, Bobin
    Yao, Wei
    Xia, Xiao-Feng
    Wang, Dawei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (24) : 4547 - 4557
  • [6] Enantioselective 1,6-Conjugate Addition of Dialkyl α-Diazo Methylphosphonate to para-Quinone Methides
    Chen, Yuan
    Yu, Rui
    Wang, Min
    Huang, Yanmin
    Peng, Yungui
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (21) : 4856 - 4861
  • [7] Base-promoted 1,6-conjugate addition of alkylazaarenes to para-quinone methides
    Rayaroth, Amritha
    Singh, Rajat Kumar
    Kalyanakrishnan, A., V
    Hari, Krishna
    Katiyamoorthy, Alagiri
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (17) : 3354 - 3359
  • [8] Copper-catalyzed 1,6-conjugate addition of para-quinone methides with diborylmethane
    Li, Xin
    Gao, Guoliang
    He, Songtao
    Song, Qiuling
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (16) : 4543 - 4548
  • [9] Asymmetric Catalytic 1,6-Conjugate Addition/Aromatization of para-Quinone Methides: Enantioselective Introduction of Functionalized Diarylmethine Stereogenic Centers
    Chu, Wen-Dao
    Zhang, Le-Fen
    Bao, Xu
    Zhao, Xian-He
    Zeng, Chao
    Du, Ji-Yuan
    Zhang, Guo-Biao
    Wang, Fang-Xin
    Ma, Xiao-Yan
    Fan, Chun-An
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) : 9229 - 9233
  • [10] Copper-catalyzed asymmetric 1,6-conjugate addition of in situ generated para-quinone methides with β-ketoesters
    Wang, Yi-Feng
    Wang, Chao-Jie
    Feng, Qing-Zhou
    Zhai, Jing-Jing
    Qi, Suo-Suo
    Zhong, Ai-Guo
    Chu, Ming-Ming
    Xu, Dan-Qian
    CHEMICAL COMMUNICATIONS, 2022, 58 (46) : 6653 - 6656