Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron

被引：56
|
作者：
Zhou, Mingkang [1 ]
Li, Kaidi [1 ]
Chen, Dongping [1 ]
Xu, Ronghua [1 ]
Xu, Guangqing [1 ,2 ]
Tang, Wenjun [1 ,2 ,3 ]
机构：
[1] Univ Chinese Acad Sci, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
[2] NingBo Zejun Pharmaceut Technol Co Ltd, Ningbo 315336, Peoples R China
[3] Univ Chinese Acadclny Sci, Sch Chem & Mat Sci, Hangzhou Inst Adv Study, Hangzhou 310024, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2020年 / 142卷 / 23期
关键词：
ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; VICINAL DIAMINES; BORONIC ESTERS; CATALYSIS; ISOQUINOLINES; EPOXIDATION; DIBORATION; BORYLATION; COMPLEXES;
D O I：
10.1021/jacs.0c04558
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method signifies the generality of diboron-enabled [3,3]-sigmatropic rearrangement.
引用
收藏
页码：10337 / 10342
页数：6
相关论文
共 50 条
  • [1] Enantioselective Nickel-Catalyzed Reductive Coupling of Alkynes and Imines
    Zhou, Chang-Yue
    Zhu, Shou-Fei
    Wang, Li-Xin
    Zhou, Qi-Lin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (32) : 10955 - 10957
  • [2] Mechanistic insights into asymmetric reductive coupling of isoquinolines by a chiral diboron with DFT calculations
    Zhou, Qinghai
    Tang, Wenjun
    Chung, Lung Wa
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 864 : 97 - 104
  • [3] Practical and Asymmetric Reductive Coupling of Isoquinolines Templated by Chiral Diborons
    Chen, Dongping
    Xu, Guangqing
    Zhou, Qinghai
    Chung, Lung Wa
    Tang, Wenjun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (29) : 9767 - 9770
  • [4] New C2-bridged diamines via reductive coupling of imines using diboron compounds
    Cameron, TM
    Baker, RT
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 215 : U787 - U787
  • [5] Diastereoselective and Enantioselective Nickel-Catalyzed Reductive Coupling of Imines and Unactivated Alkenes
    Wang, Biao
    Liu, Xian-Ming
    Zhang, Kai-Xiang
    Feng, Wei-Min
    Xiao, Li-Jun
    Zhou, Qi-Lin
    CCS CHEMISTRY, 2023, 5 (04): : 814 - 822
  • [6] Copper-Catalyzed Enantioselective Reductive Cross-Coupling of Aldehydes and Imines
    Mitsui, Atsuhisa
    Nagao, Kazunori
    Ohmiya, Hirohisa
    ORGANIC LETTERS, 2020, 22 (03) : 800 - 803
  • [7] Regioselective and Enantioselective Nickel-Catalyzed Intermolecular Reductive Coupling of Aliphatic Alkenes with Imines
    Chen, Zhi-Hong
    Gu, Li-Jie
    Wang, Biao
    Xiao, Li-Jun
    Ye, Mengchun
    Zhou, Qi-Lin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (22) : 14915 - 14921
  • [8] Asymmetric Synthesis of Vicinal Tetrasubstituted Diamines via Reductive Coupling of Ketimines Templated by Chiral Diborons
    Zhou, Mingkang
    Lin, Yaodong
    Chen, Xiao-Xuan
    Xu, Guangqing
    Chung, Lung Wa
    Tang, Wenjun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (17)
  • [9] Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides
    Agrawal, Toolika
    Martin, Robert T.
    Collins, Stephen
    Wilhelm, Zachary
    Edwards, Mytia D.
    Gutierrez, Osvaldo
    Sieber, Joshua D.
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (07): : 5026 - 5046
  • [10] Highly enantioselective allylation of imines with a chiral zirconium catalyst
    Gastner, T
    Ishitani, H
    Akiyama, R
    Kobayashi, S
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (10) : 1896 - 1898
12345