Organocatalytic cascade 1,6-conjugate addition/annulation/tautomerization of functionalized para-quinone methides: Access to chiral 2-amino-4-aryl-4H-chromenes

被引:2
|
作者
Cong Duan [1 ]
Ling Ye [2 ]
Wenqin Xu [1 ]
Xinying Li [1 ]
Feng Chen [1 ]
Zhigang Zhao [1 ]
Xuefeng Li [1 ]
机构
[1] College of Chemistry and Environment Protection Engineering, Southwest Minzu University
[2] Faculty of Geosciences and Environmental Engineering, Southwest Jiaotong University
基金
中央高校基本科研业务费专项资金资助; 中国国家自然科学基金;
关键词
para-Quinone methides; 2-Amino-4-aryl-4H-chromene; Domino reaction; 1,6-Conjugated addition; Enantioselective;
D O I
暂无
中图分类号
O625.6 [芳香族含氮化合物];
学科分类号
070303 ; 081704 ;
摘要
A novel organocatalytic cascade process initiated by 1,6-conjugated addition has been successfully developed. A range of pharmaceutically active 2-amino-4-aryl-4H-chromenes were readily obtained in high yields(88%-99%) and excellent enantiopurities(86%-99% ee). The functionalized para-Quinone methides(p-OMs) could be facilely obtained.
引用
收藏
页码:1273 / 1276
页数:4
相关论文
共 50 条
  • [1] Organocatalytic cascade 1,6-conjugate addition/annulation/tautomerization of functionalized para-quinone methides: Access to chiral 2-amino-4-aryl-4H-chromenes
    Duan, Cong
    Ye, Ling
    Xu, Wenqin
    Li, Xinying
    Chen, Feng
    Zhao, Zhigang
    Li, Xuefeng
    CHINESE CHEMICAL LETTERS, 2018, 29 (08) : 1273 - 1276
  • [2] 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
  • [3] 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
  • [4] 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
  • [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 1,6-Conjugate Addition of para-Quinone Methides for the Synthesis of Chiral β,β-Diaryl-α-Hydroxy Ketones
    Gao, Yuan-Yuan
    Hua, Yuan-Zhao
    Wang, Min-Can
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (01) : 80 - 85
  • [10] Asymmetric Organocatalytic 1,6-Conjugate Addition of para-Quinone Methides Using [1,2]-Phospha-Brook Rearrangement
    Tan, Qingfa
    Guo, Ning
    Yang, Linhan
    Wang, Fei
    Feng, Xiaoming
    Liu, Xiaohua
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13): : 9332 - 9342