Rhodium(I)-Catalyzed 1,4-Addition of Arylboronic Acids to Acrylic Acid in Water: One-Step Preparation of 3-Arylpropionic Acids

被引:12
|
作者
Vautravers, Nicolas R. [1 ]
Breit, Bernhard [1 ]
机构
[1] Univ Freiburg, Inst Organ Chem & Biochem, Freiburg Inst Adv Studies FRIAS, D-79104 Freiburg, Germany
关键词
boronic acids; acrylic acid; water; conjugate addition; rhodium; CATALYZED ASYMMETRIC 1,4-ADDITION; CONJUGATE ADDITION; ENANTIOSELECTIVE DESYMMETRIZATION; ALLYLIC AMINES; BORONIC ACIDS; RHODIUM; ALKYNES; HETEROCYCLES; REAGENTS; LIGANDS;
D O I
10.1055/s-0030-1260319
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical method for the one-step preparation of 3-arylpropionic acids through rhodium-catalyzed 1,4-addition of arylboronic acids to acrylic acid is reported. The method is applicable to a broad scope of aryl boronic acids and displays a wide functional group tolerance operating in water as the optimal reaction medium.
引用
收藏
页码:2517 / 2520
页数:4
相关论文
共 50 条
  • [21] Chiral norbornadienes as efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds
    Shintani, R
    Ueyama, K
    Yamada, I
    Hayashi, T
    ORGANIC LETTERS, 2004, 6 (19) : 3425 - 3427
  • [22] Preparation of chiral 7,7′-disubstituted BINAPs for Rh-catalyzed 1,4-addition of arylboronic acids
    Yuan, WC
    Cun, LF
    Gong, LZ
    Mi, AQ
    Jiang, YZ
    TETRAHEDRON LETTERS, 2005, 46 (03) : 509 - 512
  • [23] Preparation of Chiral 3-Arylpyrrolidines via the Enantioselective 1,4-Addition of Arylboronic Acids to Fumaric Esters Catalyzed by Rh(I)/Chiral Diene Complexes
    Chung, Yu-Chiang
    Janmanchi, Damodar
    Wu, Hsyueh-Liang
    ORGANIC LETTERS, 2012, 14 (11) : 2766 - 2769
  • [24] Rhodium catalyzed asymmetric 1,4-addition of arylboronic acids to β,γ-unsaturated α-keto ester using chiral tert-butanesulfinylphosphines ligands
    Wang, Juanjuan
    Wang, Bing
    Cao, Peng
    Liao, Jian
    TETRAHEDRON LETTERS, 2014, 55 (23) : 3450 - 3453
  • [25] Rhodium-catalyzed asymmetric 1,4-addition of aryl- and alkenylboronic acids to enones
    Takaya, Y
    Ogasawara, M
    Hayashi, T
    Sakai, M
    Miyaura, N
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) : 5579 - 5580
  • [26] Highly Enantioselective Rhodium-Catalyzed Asymmetric 1,4-Addition Reactions of Arylboronic Acids to Acyclic α,β-Unsaturated Compounds: The Formal Synthesis of (-)-Indatraline
    Wei, Wei-Ting
    Yeh, Jiann-Yih
    Kuo, Ting-Shen
    Wu, Hsyueh-Liang
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (41) : 11405 - 11409
  • [27] Rhodium/Chiral Diene-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Chromones: A Highly Enantioselective Pathway for Accessing Chiral Flavanones
    He, Qijie
    So, Chau Ming
    Bian, Zhaoxiang
    Hayashi, Tamio
    Wang, Jun
    CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (03) : 540 - 543
  • [28] Rh-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Ketones with DIFLUORPHOS and SYNPHOS Analogues
    Berhal, Farouk
    Wu, Zi
    Genet, Jean-Pierre
    Ayad, Tahar
    Ratovelomanana-Vidal, Virginie
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (15): : 6320 - 6326
  • [29] Wide bite angle diphosphine rhodium complexes: Synthesis, structure, and catalytic 1,4-addition of arylboronic acids to enones
    Morgan, Brad P.
    Smith, Rhett C.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (01) : 11 - 16
  • [30] Tandem 1,4-addition/enantioselective protonation catalyzed by rhodium complexes:: Efficient access to α-amino acids
    Navarre, L
    Darses, S
    Genet, JP
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (06) : 719 - 723