Fe(OTf)3-Catalyzed Synthesis of Boronic Ester Containing N,O-Acetal Structure

被引：0
|
作者：
Lu Min [1 ,2 ]
Yang Aimei [1 ]
Zhang Yu [1 ,2 ]
Sun Jianting [2 ]
Wei Bangguo [2 ]
机构：
[1] Lanzhou Univ Technol, Sch Life Sci & Engn, Lanzhou 730050, Peoples R China
[2] Fudan Univ, Sch Pharm, Shanghai 201203, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 43卷 / 05期
基金：
中国国家自然科学基金;
关键词：
iminonium; N; O-acetal; boronic ester; addition reaction; CROSS-COUPLING REACTION; REGIOSELECTIVE GLYCOSYLATION; ASYMMETRIC-SYNTHESIS; IXAZOMIB CITRATE; TRANSESTERIFICATION; DERIVATIVES; CHEMISTRY; ACIDS;
D O I：
10.6023/cjoc202301017
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient approach acess to boronic ester containing N,O-acetal structure has been established through the Fe(OTf)(3)-catalyzed addition of N,O-acetal with organic boric acid. A series of N-O-acetal boronic ester compounds have been successfully prepared in 58%similar to 98% yields. Moreover, these compounds retain the property of boronic ester and can be used for coupling reaction.
引用
收藏
页码：1777 / 1785
页数：9
相关论文
共 64 条
  • [1] A supramolecular nanoprodrug based on a boronate ester linked curcumin complexing with water-soluble pillar[5]arene for synergistic chemotherapies
    Chao, Shuang
    Lv, Xiukai
    Ma, Ning
    Shen, Ziyan
    Zhang, Feiyu
    Pei, Yuxin
    Pei, Zhichao
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (62) : 8861 - 8864
  • [2] Recent Advances in the Palladium Catalyzed Suzuki-Miyaura Cross-Coupling Reaction in Water
    Chatterjee, Anamitra
    Ward, Thomas R.
    [J]. CATALYSIS LETTERS, 2016, 146 (04) : 820 - 840
  • [3] A One-Pot Approach to 2-Substituted-2-(Dimethoxyphosphoryl)-Pyrrolidines from Substituted tert-Butyl 4-Oxobutylcarbamates and Trimethyl Phosphite
    Chen, Zhao-Dan
    Xu, Wen-Ke
    Guo, Jia-Ming
    Chen, Ling
    Wei, Bang-Guo
    Si, Chang-Mei
    Lin, Guo-Qiang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (17) : 11442 - 11455
  • [4] Stereoselective approach to access 3-tert-Butyl-Dimethylsiloxy-2,6-Substituted piperidines through nucleophilic addition of N,O-acetals with organozinc reagents
    Chen, Zhao-Dan
    Chen, Zhuo
    Wang, Qiao-E
    Sia, Chang-Mei
    Wei, Bang-Guo
    [J]. TETRAHEDRON LETTERS, 2020, 61 (26)
  • [5] Tavaborole, a Novel Boron-Containing Small Molecule Pharmaceutical Agent for Topical Treatment of Onychomycosis: I. Reproductive and Developmental Toxicity Studies
    Ciaravino, Vic
    Coronado, Dina
    Lanphear, Cheryl
    Hoberman, Alan
    Chanda, Sanjay
    [J]. INTERNATIONAL JOURNAL OF TOXICOLOGY, 2016, 35 (05) : 530 - 542
  • [6] Boron-Containing heterocycles as promising pharmacological agents
    Das, Bhaskar C.
    Shareef, Mohammed Adil
    Das, Sasmita
    Nandwana, Nitesh K.
    Das, Yogarupa
    Saito, Mariko
    Weiss, Louis M.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2022, 63
  • [7] Dynamic Combinatorial Chemistry Employing Boronic Acids/Boronate Esters Leads to Potent Oxygenase Inhibitors
    Demetriades, Marina
    Leung, Ivanhoe K. H.
    Chowdhury, Rasheduzzaman
    Chan, Mun Chiang
    McDonough, Michael A.
    Yeoh, Kar Kheng
    Tian, Ya-Min
    Claridge, Timothy D. W.
    Ratcliffe, Peter J.
    Woon, Esther C. Y.
    Schofield, Christopher J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (27) : 6672 - 6675
  • [8] Organoboron Acids and Their Derivatives as Catalysts for Organic Synthesis
    Dimitrijevic, Elena
    Taylor, Mark S.
    [J]. ACS CATALYSIS, 2013, 3 (05): : 945 - 962
  • [9] Boron acids as protective agents and catalysts in synthesis
    Duggan, PJ
    Tyndall, EM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (11): : 1325 - 1339
  • [10] Asymmetric Allylation of N,O-Acetal and Application in the Synthesis of Epiquinamide and (+)-Febrifugine
    Feng, Tao
    Si, Changmei
    Liu, Rucheng
    Fan, Xiang
    Wei, Bangguo
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (06) : 1291 - 1297
1234567