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
  • [41] Enantioselective Cobalt-Catalyzed Reductive Cross-Coupling for the Synthesis of Axially Chiral Phosphine-Olefin Ligands
    Zhang, Xi
    Wang, Juan
    Yang, Shang-Dong
    ACS CATALYSIS, 2021, 11 (22) : 14008 - 14015
  • [42] Enantioselective Copper-Catalyzed Reductive Coupling of Alkenylazaarenes with Ketones
    Saxena, Aakarsh
    Choi, Bonnie
    Lam, Hon Wai
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (20) : 8428 - 8431
  • [43] Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes
    Horwitz, Matthew A.
    Tanaka, Naoya
    Yokosaka, Takuya
    Uraguchi, Daisuke
    Johnson, Jeffrey S.
    Ooi, Takashi
    CHEMICAL SCIENCE, 2015, 6 (11) : 6086 - 6090
  • [44] Development of chiral catalysts by asymmetric activation for highly enantioselective diethylzinc addition to imines
    Zhang, HL
    Liu, H
    Cui, X
    Mi, AQ
    Jiang, YZ
    Gong, LZ
    SYNLETT, 2005, (04) : 615 - 618
  • [45] Copper-hydride catalyzed diastereo- and enantioselective synthesis of homopropargyl amines through reductive coupling of 1,3-enynes with imines
    Su, Ting
    Li, Mingfeng
    Meng, Fanke
    Chong, Qinglei
    TETRAHEDRON, 2025, 176
  • [46] Stereoselective oxidative and reductive coupling using chiral auxiliaries
    Kise, N
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2004, 62 (04) : 306 - 313
  • [47] The enantioselective diethylzinc addition to imines catalyzed by chiral Cu(II)-oxazoline complexes
    Li, X
    Cun, LF
    Gong, LZ
    Mi, AQ
    Jiang, YZ
    TETRAHEDRON-ASYMMETRY, 2003, 14 (24) : 3819 - 3821
  • [48] An entry to a chiral dihydropyrazole scaffold: Enantioselective [3 + 2] cycloaddition of nitrile imines
    1600, American Chemical Society, Columbus, United States (127):
  • [49] Enantioselective addition of oxazolones to N-protected imines catalysed by chiral thioureas
    Zabka, Matej
    Malastova, Andrea
    Sebesta, Radovan
    RSC ADVANCES, 2015, 5 (17): : 12890 - 12893
  • [50] Catalytic, enantioselective allylation of α-iminoesters promoted by silver(I) complexes of chiral imines
    Colombo, Federica
    Annunziata, Rita
    Benaglia, Maurizio
    TETRAHEDRON LETTERS, 2007, 48 (15) : 2687 - 2690