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
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
  • [31] Enantioselective preparation and chemoselective cross-coupling of 1,1-diboron compounds
    Jack Chang Hung Lee
    Robert McDonald
    Dennis G. Hall
    Nature Chemistry, 2011, 3 : 894 - 899
  • [32] Reductive coupling of ketones with imines promoted by the titanium tetrachloride/samarium system
    Ma, YM
    Zhang, YM
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2000, 32 (06) : 567 - 570
  • [33] Enantioselective Preparation and Chemoselective Cross-Coupling of 1,1-Diboron Compounds
    Zanda, Matteo
    SYNLETT, 2012, (04) : A22 - A25
  • [34] Molybdenum η2-imine complex formation and the reductive coupling of imines
    Cameron, TM
    Ortiz, CG
    Abboud, KA
    Boncella, JM
    Baker, RT
    Scott, BL
    CHEMICAL COMMUNICATIONS, 2000, (07) : 573 - 574
  • [35] Reductive coupling between aromatic aldehydes and ketones or imines by copper catalysis
    Takeda, Mitsutaka
    Mitsui, Atsuhisa
    Nagao, Kazunori
    Ohmiya, Hirohisa
    Journal of the American Chemical Society, 2019, 141 (08): : 3664 - 3669
  • [36] Reductive Coupling between Aromatic Aldehydes and Ketones or Imines by Copper Catalysis
    Takeda, Mitsutaka
    Mitsui, Atsuhisa
    Nagao, Kazunori
    Ohmiya, Hirohisa
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (08) : 3664 - 3669
  • [37] Samarium-promoted diastereoselective reductive coupling of optically active imines
    Yanada, R
    Negoro, N
    Okaniwa, M
    Miwa, Y
    Taga, T
    Yanada, K
    Fujita, T
    SYNLETT, 1999, (05) : 537 - 540
  • [38] REDUCTIVE COUPLING IN SUBSTITUTED IMINES WITH ALUMINUM-AMALGAM IN MOIST ETHER
    JOSHI, SC
    MEHROTRA, KN
    NATIONAL ACADEMY SCIENCE LETTERS-INDIA, 1980, 3 (09): : 268 - 272
  • [39] Enantioselective Reductive (Hetero)Arylation of Cyclic N-Sulfonyl Imines by Cobalt Catalysis
    Xiao, Jieshuai
    Wang, Minyan
    Yin, Xuwen
    Yang, Shuo
    Gu, Pei
    Lv, Xueli
    Zhao, Yue
    Shi, Zhuangzhi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (19)
  • [40] Enantioselective construction of C-B axially chiral alkenylborons by nickel-catalyzed radical relayed reductive coupling
    Qiu, Weihua
    Tao, Rencai
    He, Yong
    Zhou, Yao
    Yang, Kai
    Song, Qiuling
    NATURE COMMUNICATIONS, 2024, 15 (01)