Regioselective and Stereoselective Entry to β,β-Disubstituted Vinyl Ethers via the Sequential Hydroboration/Suzuki-Miyaura Coupling of Ynol Ethers

被引：21
作者：
Cui, Weijian [1 ]
Mao, Mengyi [1 ]
He, Zuying [1 ]
Zhu, Gangguo [1 ]
机构：
[1] Zhejiang Normal Univ, Dept Chem, Jinhua 321004, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 19期
基金：
中国国家自然科学基金;
关键词：
ARYL ETHYNYL ETHERS; TERMINAL ALKYNES; ENOL ETHERS; CATALYZED HYDROBORATION; CONVENIENT SYNTHESIS; CARBONYL-COMPOUNDS; ALLYL; CYCLOADDITION; ESTERS; REARRANGEMENT;
D O I：
10.1021/jo401523m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly regio- and stereoselective synthesis of stereodefined beta,beta-disubstituted alkenyl ethers featuring the sequential hydroboration/Suzuki-Miyaura coupling of ynol ethers has been described. A number of functional groups, including OMe, Ac, CO2Et, CN, halides, and alkyl, (hetero)aryl, and alkenyl groups, are well-tolerated under the reaction conditions. Furthermore, it allows a facile entry to the labile diarylacetaldehydes by TFA-mediated hydrolysis of beta,beta-disubstituted vinyl ethers.
引用
收藏
页码：9815 / 9821
页数：7
相关论文
共 59 条
  • [1] Synthesis of seven-membered ring glycals via endo-selective alkynol cycloisomerization
    Alcázar, E
    Pletcher, JM
    McDonald, FE
    [J]. ORGANIC LETTERS, 2004, 6 (21) : 3877 - 3880
  • [2] Pd-catalyzed addition of boronic acids to ynol ethers: a highly regio- and stereoselective synthesis of trisubstituted vinyl ethers
    Bai, Yihui
    Yin, Jing
    Kong, Wei
    Mao, Mengyi
    Zhu, Gangguo
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (69) : 7650 - 7652
  • [3] Synthesis of Enol Ethers and Enamines by Pd-Catalyzed Tosylhydrazide-Promoted Cross-Coupling Reactions
    Barluenga, Jose
    Escribano, Maria
    Moriel, Patricia
    Aznar, Fernando
    Valdes, Carlos
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (48) : 13291 - 13294
  • [4] Hydroborations catalysed by transition metal complexes
    Beletskaya, I
    Pelter, A
    [J]. TETRAHEDRON, 1997, 53 (14) : 4957 - 5026
  • [5] Brown H.C., 1981, ALDRICHIM ACTA, V14, P3
  • [6] Palladium-catalyzed haloallylation of aromatic ynol ethers with allyl chlorides: a highly regio- and stereoselective approach to (1E)-α-chloroenol ethers
    Cai, Haiting
    Yuan, Zheliang
    Zhu, Weidong
    Zhu, Gangguo
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (30) : 8682 - 8684
  • [7] Synthesis of cis-1,2-Dihaloalkenes Featuring Palladium-Catalyzed Coupling of Haloalkynes and α,β-Unsaturated Carbonyls
    Chen, Dongxu
    Cao, Yi
    Yuan, Zheliang
    Cai, Haiting
    Zheng, Renwei
    Kong, Lichun
    Zhu, Gangguo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10) : 4071 - 4074
  • [8] Palladium-Catalyzed Coupling of Haloalkynes with Allyl Acetate: A Regio- and Stereoselective Synthesis of (Z)-β-Haloenol Acetates
    Chen, Xiaoyi
    Chen, Dongxu
    Lu, Zenghui
    Kong, Lichun
    Zhu, Gangguo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (15) : 6338 - 6343
  • [9] Palladium-catalyzed highly regio- and stereoselective synthesis of (1E)- or (1Z)-1,2-dihalo-1,4-dienes via haloallylation of alkynyl halides
    Chen, Xiaoyi
    Kong, Wei
    Cai, Haiting
    Kong, Lichun
    Zhu, Gangguo
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (07) : 2164 - 2166
  • [10] Intermolecular and Selective Synthesis of 2,4,5-Trisubstituted Oxazoles by a Gold-Catalyzed Formal [3+2] Cycloaddition
    Davies, Paul W.
    Cremonesi, Alex
    Dumitrescu, Lidia
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (38) : 8931 - 8935
123456