Chiral dihydroxytetraphenylene-catalyzed enantioselective conjugate addition of boronic acids to β-enaminones

被引:13
|
作者
Yao, En-Ze [1 ]
Chai, Guo-Li [1 ]
Zhang, Ping [1 ]
Zhu, Bo [1 ]
Chang, Junbiao [1 ]
机构
[1] Henan Normal Univ, Sch Chem & Chem Engn, NMPA Key Lab Res & Evaluat Innovat Drug, Henan Key Lab Organ Funct Mol & Drug Innovat, Xinxiang 453007, Henan, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 09期
基金
中国国家自然科学基金;
关键词
ASYMMETRIC DARZENS REACTION; BOND-FORMING REACTIONS; ALKENYLBORONIC ACIDS; ARYLBORONIC ACIDS; ENONES; AMIDES; CONSTRUCTION; COMPLEXES; MOTUPORIN; CHEMISTRY;
D O I
10.1039/d1qo01845k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report the (S)-2,15-Cl-2-DHTP-catalyzed enantioselective conjugate addition of organic boronic acids to beta-enaminones, providing the corresponding addition products in high yields and moderate to excellent enantioselectivities (up to 98% ee). This catalytic system exhibits unique features in terms of mild reaction conditions, high efficiency, broad substrate scope, and the applicability of alkenylboronic acids and heteroarylboronic acids.
引用
收藏
页码:2375 / 2381
页数:7
相关论文
共 50 条
  • [1] Highly Enantioselective Chiral Diol-Catalyzed Conjugate Addition of Boronic Acids to α,β-Unsaturated Trifluoromethyl Ketones
    Hou, Ya-Jing
    Zhao, Lu
    Chai, Guo-Li
    Zhong, Kangbao
    Chang, Junbiao
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (24): : 17461 - 17471
  • [2] Enantioselective Conjugate Addition of Boronic Acids to α,β-Unsaturated 2-Acyl Imidazoles Catalyzed by Chiral Diols
    Chai, Guo-Li
    Zhang, Ping
    Yao, En-Ze
    Chang, Junbiao
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (14): : 9197 - 9209
  • [3] 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
  • [4] Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones
    Chai, Guo-Li
    Sun, A-Qiang
    Zhai, Dong
    Wang, Juan
    Deng, Wei-Qiao
    Wong, Henry N. C.
    Chang, Junbiao
    ORGANIC LETTERS, 2019, 21 (13) : 5040 - 5045
  • [5] Organocatalyzed Enantioselective Conjugate Addition of Boronic Acids to β,γ-Unsaturated α-Ketoesters
    Zhao, Lu
    Yao, En-Ze
    Chai, Guo-Li
    Ma, Shi-Yu
    Chang, Junbiao
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (24): : 18211 - 18223
  • [6] Readily Accessible Chiral Diene Ligands for Rh-Catalyzed Enantioselective Conjugate Additions of Boronic Acids
    Trost, Barry M.
    Burns, Aaron C.
    Tautz, Thomas
    ORGANIC LETTERS, 2011, 13 (17) : 4566 - 4569
  • [7] Palladium-catalyzed enantioselective conjugate addition of arylboronic acids
    Gini, F
    Hessen, B
    Minnaard, AJ
    ORGANIC LETTERS, 2005, 7 (23) : 5309 - 5312
  • [8] Enantioselective Conjugate Addition of Fluoromalonate to Nitroalkenes Catalyzed by Chiral Nickel Complexes
    Kang, Seung Hee
    Kim, Dae Young
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2009, 30 (07): : 1439 - 1440
  • [9] Enantioselective conjugate addition of pyrazolones to nitroalkenes catalyzed by chiral squaramide organocatalyst
    Aydin, Alime Ebru
    Culha, Selda
    CHIRALITY, 2021, 33 (03) : 106 - 114
  • [10] Chiral amides via copper-catalyzed enantioselective conjugate addition
    Schoonen, Anne K.
    Fernandez-Ibanez, Maria A.
    Fananas-Mastral, Martin
    Teichert, Johannes F.
    Feringa, Ben L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248