Asymmetric synthesis of stable α-aminoboronic esters catalyzed by N-heterocylic carbene and copper(I) chloride

被引：13
|
作者：
Chen, Jinbo [1 ]
Chen, Ling-yan [1 ]
Zheng, Yue [1 ]
Sun, Zhihua [1 ]
机构：
[1] Shanghai Univ Engn Sci, Coll Chem & Chem Engn, Shanghai 201620, Peoples R China
来源：
RSC ADVANCES | 2014年 / 4卷 / 40期
关键词：
DIPEPTIDYL PEPTIDASE-IV; AMINO BORONATE ESTERS; PROTEASOME INHIBITORS; LIGANDS; ACTIVATION; ALDIMINES; COMPLEX; TARGET; CANCER; BOND;
D O I：
10.1039/c4ra02229g
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Bis(pinanediolato)diboron (B(2)pnd(2)) was used as the nucleophile instead of bis(pinacolato)diboron in the stereospecific synthesis of alpha-aminoboronic esters catalysed by a triazole-based N-hetereocyclic carbene (NHC) and Cu(I) chloride. The resulting pinanediol-protected alpha-aminoboronic esters have significantly improved stability over the pinacol derivatives.
引用
收藏
页码：21131 / 21133
页数：3
相关论文
共 50 条
  • [41] SYNTHESIS OF ENANTIOENRICHED INDOLOPIPERAZINONES VIA IRIDIUM(I) N-HETEROCYCLIC CARBENE COMPLEX CATALYZED ASYMMETRIC INTRAMOLECULAR ALLYLIC AMINATION REACTION
    Ye, Ke-Yin
    Wu, Ke-Jia
    Li, Guo-Tai
    Dai, Li-Xin
    You, Shu-Li
    HETEROCYCLES, 2017, 95 (01) : 304 - 313
  • [42] N-heterocyclic carbene-catalyzed oxidation of aldehydes for the synthesis of amides via phenolic esters
    Ji, Miran
    Lim, Seungyeon
    Jang, Hye-Young
    RSC ADVANCES, 2014, 4 (54) : 28225 - 28228
  • [43] Copper(I)-Catalyzed Asymmetric [3+2]-Cycloaddition of α-Substituted Iminoesters with α-Trifluoromethyl α,β-Unsaturated Esters
    Xu, Shan
    Liu, Bing
    Zhang, Zhan-Ming
    Xu, Bing
    Zhang, Junliang
    CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (05) : 421 - 429
  • [44] Stannyl cyclopropanes by diastereoselective cyclopropanations with (tributylstannyl)-diazoacetate esters catalyzed by Cu(I) N-heterocyclic carbene
    Gawley, RE
    Narayan, S
    CHEMICAL COMMUNICATIONS, 2005, (40) : 5109 - 5111
  • [45] Chiral N-Heterocyclic Carbene-Copper(I)-Catalyzed Asymmetric Allylic Arylation of Aliphatic Allylic Bromides: Steric and Electronic Effects on γ-Selectivity
    Selim, Khalid B.
    Nakanishi, Hirotsugu
    Matsumoto, Yasumasa
    Yamamoto, Yasutomo
    Yamada, Ken-ichi
    Tomioka, Kiyoshi
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05): : 1398 - 1408
  • [46] N-Heterocyclic Carbene Catalyzed Quadruple Domino Reactions: Asymmetric Synthesis of Cyclopenta[c]chromenones
    Liu, Qiang
    Chen, Xiang-Yu
    Puttreddy, Rakesh
    Rissanen, Kari
    Enders, Dieter
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (52) : 17100 - 17103
  • [47] N-Heterocyclic Carbene Complexes of Copper(I) Thiocyanate: Synthesis and Structural Characterization
    Dodds, Christopher A.
    Kennedy, Alan R.
    ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2014, 640 (05): : 926 - 930
  • [48] Aerobic synthesis of N-sulfonylamidines mediated by N-heterocyclic carbene copper(I) catalysts
    Lazreg, Falima
    Vasseur, Marie
    Slawin, Alexandra M. Z.
    Cazin, Catherine S. J.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 482 - 491
  • [49] Copper(I)-Catalyzed Asymmetric Interrupted Kinugasa Reaction: Synthesis of α-Thiofunctional Chiral β-Lactams
    Qi, Jialin
    Wei, Fang
    Huang, Shuai
    Tung, Chen-Ho
    Xu, Zhenghu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (09) : 4561 - 4565
  • [50] Copper(I) Iodide-Catalyzed Asymmetric Synthesis of Optically Active Tertiary -Allenols
    Liu, Qi
    Cao, Tao
    Han, Yulin
    Jiang, Xingguo
    Tang, Yang
    Zhai, Yizhan
    Ma, Shengming
    SYNLETT, 2019, 30 (04) : 477 - 482
12345