Stereoselective synthesis of α-allenols by rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids

被引:75
|
作者
Miura, Tomoya
Shimada, Masahiko
Ku, Sung-Yu
Tamai, Tomohiro
Murakami, Masahiro
机构
[1] Kyoto Univ, Dept Synth Chem & Biolog Chem, Kyoto 6159510, Japan
[2] Natl Taiwan Univ, Dept Chem, Taipei, Taiwan
关键词
beta-oxygen elimination; addition; allenes; boron; rhodium;
D O I
10.1002/anie.200701505
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Better than Cu, Pd, and Fe catalysts: The rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids provides synconfigured α-allenols with excellent diastereoselectivity. Precoordination of the oxygen atom of the oxirane ring to rhodium is assumed to contribute to the high stereoselectivity as well as high reactivity. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7101 / 7103
页数:3
相关论文
共 50 条
  • [41] Rhodium-catalyzed enantioselective 1,4-additions of arylboronic acids to substituted enones
    Urbaneja, LM
    Krause, N
    TETRAHEDRON-ASYMMETRY, 2006, 17 (04) : 494 - 496
  • [42] Rhodium-catalyzed formal [2+2+1] annulation of arylboronic acids with alkynes
    Wang, Chenhong
    Wu, Changhui
    Yang, Yiming
    Xing, Junhao
    Dou, Xiaowei
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (24) : 6915 - 6919
  • [43] Direct Synthesis of Chiral 3-Arylsuccinimides by Rhodium-Catalyzed Enantioselective Conjugate Addition of Arylboronic Acids to Maleimides
    Gopula, Balraj
    Yang, Shu-Han
    Kuo, Ting-Shen
    Hsieh, Jen-Chieh
    Wu, Ping-Yu
    Henschke, Julian P.
    Wu, Hsyueh-Liang
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (31) : 11050 - 11055
  • [44] Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: Asymmetric synthesis of (R)-tolterodine
    Chen, G
    Tokunaga, N
    Hayashi, T
    ORGANIC LETTERS, 2005, 7 (11) : 2285 - 2288
  • [45] Rhodium-catalyzed cyclization of 1,6-enynes triggered by addition of arylboronic acids
    Miura, T
    Shimada, M
    Murakami, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) : 1094 - 1095
  • [46] Rhodium-Catalyzed Highly Enantioselective Addition of Arylboronic Acids to Cyclic Aldimines: Practical Asymmetric Synthesis of Cyclic Sulfamidates
    Wang, Hui
    Xu, Ming-Hua
    SYNTHESIS-STUTTGART, 2013, 45 (15): : 2125 - 2133
  • [47] Rhodium-Catalyzed Dealkenylative Arylation of Alkenes with Arylboronic Compounds
    Tan, Guangying
    Das, Mowpriya
    Maisuls, Ivan
    Strassert, Cristian A.
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (28) : 15650 - 15655
  • [48] Palladium-catalyzed coupling reaction of propargylic oxiranes with arylboronic acids in aqueous media
    Yoshida, M
    Ueda, H
    Ihara, M
    TETRAHEDRON LETTERS, 2005, 46 (39) : 6705 - 6708
  • [49] 2-ALKYLIDENE-1,3-DITHIANE MONOXIDES AS ACTIVATED ALKENES IN RHODIUM-CATALYZED ADDITION REACTION OF ARYLBORONIC ACIDS
    Yoshida, Suguru
    Yorimitsu, Hideki
    Oshima, Koichiro
    HETEROCYCLES, 2008, 76 (01) : 679 - 688
  • [50] Rhodium-catalyzed cyclization reaction of 1,6-enynes with arylboronic acids through β-hydride elimination/hydrorhodation sequence
    Shimada, Masahiko
    Harumashi, Tatsuro
    Miura, Tomoya
    Murakami, Masahiro
    CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (06) : 1035 - 1040