Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones

被引：39
|
作者：
Chai, Guo-Li [1 ]
Sun, A-Qiang [1 ]
Zhai, Dong [2 ]
Wang, Juan [1 ]
Deng, Wei-Qiao [1 ,2 ]
Wong, Henry N. C. [1 ,3 ]
Chang, Junbiao [1 ]
机构：
[1] Henan Normal Univ, Sch Chem & Chem Engn, Henan Key Lab Organ Funct Mol & Drug Innovat, Xinxiang 453007, Henan, Peoples R China
[2] Shandong Univ, Inst Mol Sci & Engn, Qingdao 266237, Shandong, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 13期
基金：
中国国家自然科学基金;
关键词：
ALKENYLBORONIC ACIDS; ALPHA; BETA-UNSATURATED KETONES; STEREOSELECTIVE-SYNTHESIS; 1,4-ADDITION REACTION; ALKYNYLATION; ARYL; TRIFLUOROMETHYLATION; ALKENYLATION; CONSTRUCTION; RATIONALE;
D O I：
10.1021/acs.orglett.9b01637
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(S)-2,15-Br-2-DHTP-catalyzed asymmetric conjugate addition of boronic acids to beta-trifluoromethyl alpha,beta-unsaturated ketones and enones was studied. The reaction afforded the corresponding Michael addition products in moderate to high yields with excellent enantioselectivities (up to 99:1 er). This catalytic system features mild reaction conditions, high efficiency, and tolerance to heteroarylboronic acids.
引用
收藏
页码：5040 / 5045
页数：6
相关论文
共 50 条
  • [1] Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones (vol 21, pg 5040, 2019)
    Chai, Guo-Li
    Sun, A-Qjang
    Zhai, Dong
    Wang, Juan
    Deng, Wei-Qiao
    Wong, Henry N. C.
    Chang, Junbiao
    ORGANIC LETTERS, 2019, 21 (16) : 6584 - 6584
  • [2] Enantioselective conjugate addition of boronic acids to enones catalyzed by O-monoacyltartaric acids
    Sugiura, Masaharu
    Tokudomi, Mirai
    Nakajima, Makoto
    CHEMICAL COMMUNICATIONS, 2010, 46 (41) : 7799 - 7800
  • [3] Chiral Metallacycles as Catalysts for Asymmetric Conjugate Addition of Styrylboronic Acids to α,β-Enones
    Hong, Tao
    Zhang, Zibin
    Sun, Yan
    Tao, Jia-Ju
    Tang, Jia-Dong
    Xie, Chunsong
    Wang, Min
    Chen, Fang
    Xie, Shang-Shu
    Li, Shijun
    Stang, Peter J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (23) : 10244 - 10249
  • [4] Rhodium-catalyzed asymmetric conjugate additions of boronic acids to enones using DIPHONANE: A novel chiral bisphosphine ligand
    Vandyck, K
    Matthys, B
    Willen, M
    Robeyns, K
    Van Meervelt, L
    Van der Eycken, J
    ORGANIC LETTERS, 2006, 8 (03) : 363 - 366
  • [5] Asymmetric conjugate addition of bromonitromethane to cyclic enones catalyzed by chiral monosulfonated diamines
    Du, Quan-sheng
    Dong, Li-ting
    Wang, Jin-jia
    Lu, Rui-jiong
    Yan, Ming
    ARKIVOC, 2009, : 191 - 199
  • [6] Chiral dihydroxytetraphenylene-catalyzed enantioselective conjugate addition of boronic acids to β-enaminones
    Yao, En-Ze
    Chai, Guo-Li
    Zhang, Ping
    Zhu, Bo
    Chang, Junbiao
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (09): : 2375 - 2381
  • [7] Conjugate addition of aryl boronic acids to enones catalyzed by cationic palladium(II)-phosphane complexes
    Nishikata, T
    Yamamoto, Y
    Miyaura, N
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (24) : 2768 - 2770
  • [8] Asymmetric conjugate alkenylation of enones catalyzed by chiral diols
    Wu, T. Robert
    Chong, J. Michael
    1600, American Chemical Society, Columbus, United States (129):
  • [9] Asymmetric conjugate alkenylation of enones catalyzed by chiral diols
    Wu, T. Robert
    Chong, J. Michael
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (16) : 4908 - +
  • [10] New chiral ligands for the asymmetric copper catalyzed conjugate addition of Grignard reagents to enones
    Stangeland, EL
    Sammakia, T
    TETRAHEDRON, 1997, 53 (48) : 16503 - 16510
12345