1,6-Conjugate addition of para-quinone methides using gem-diborylcarbanions: Practical access to gem-diborylalkanes bearing vicinal tertiary/quaternary stereocenters

被引：4
|
作者：
Zi, Pu-Zhang [1 ]
Liu, Xing -Bang [1 ]
Zhao, Quan-Hong [1 ]
He, Min [1 ]
Huang, Yuan [1 ]
机构：
[1] Xi An Jiao Tong Univ, Sch Pharm, Dept Med Chem, Xian 710061, Peoples R China
来源：
GREEN SYNTHESIS AND CATALYSIS | 2024年 / 5卷 / 01期
基金：
中国国家自然科学基金;
关键词：
gem-Diborylalkanes; Quaternary stereocenter; Conjugate addition; para-Quinone methides; Organoboron compounds; NATURAL-PRODUCTS; CARBON; CONSTRUCTION; 1,1-DIBORYLALKANES; DIBORYLATION; CARBANIONS; ALDEHYDES; ESTERS; BORON; ACID;
D O I：
10.1016/j.gresc.2022.12.003
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel, efficient and pragmatic method to prepare gem-diboron products with vicinal tertiary/quaternary stereocenters using LiTMP-mediated 1,6 -conjugate addition of gem-diborylalkanes to para-quinone methides was described for the first time. The results showed that various gem-diboron products with vicinal tertiary and quaternary stereocenters could be formed within 15 min at ambient temperature. This simple protocol has also been applied for the efficient synthesis of the analogue of Bedaquiline.
引用
收藏
页码：68 / 72
页数：5
相关论文
共 50 条
  • [1] Ligand-Free Copper-Catalyzed 1,6-Conjugate Reaction of para-Quinone Methides with gem-Diborylalkanes
    He, Jing
    Meng, Deyuan
    Lee, Dong Yeon
    Yun, Jaesook
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (47)
  • [2] Catalytic Asymmetric 1,6-Conjugate Addition of para-Quinone Methides: Formation of All-Carbon Quaternary Stereocenters
    Wang, Zhaobin
    Wong, Yuk Fai
    Sun, Jianwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (46) : 13711 - 13714
  • [3] 1,6-Conjugate sulfonylation of para-quinone methides: An expedient approach to unsymmetrical gem-diarylmethyl sulfones
    Guan, Xiao-Yu
    Zhang, Liang-Dong
    You, Peng-Sheng
    Liu, Sheng-Shu
    Liu, Zhang-Qin
    TETRAHEDRON LETTERS, 2019, 60 (03) : 244 - 247
  • [4] 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
  • [5] 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
  • [6] 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
  • [7] 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
  • [8] 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
  • [9] 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
  • [10] Stereoselective 1,6-Conjugate Addition/Annulation of para-Quinone Methides with Vinyl Epoxides/Cyclopropanes
    Ma, Chao
    Huang, Yuan
    Zhao, Yu
    ACS CATALYSIS, 2016, 6 (10): : 6408 - 6412
12345