Synergistic Catalysis: Enantioselective Addition of Alkylbenzoxazoles to Enals

被引:48
|
作者
Meazza, Marta [1 ]
Ceban, Victor [1 ]
Pitak, Mateusz B. [1 ]
Coles, Simon J. [1 ]
Rios, Ramon [1 ]
机构
[1] Univ Southampton, Fac Nat & Environm Sci, Southampton SO17 1BJ, Hants, England
基金
英国工程与自然科学研究理事会;
关键词
alkyl azaarenes; iminium catalysis; Michael addition; palladium; synergistic catalysis; TRANSITION-METAL CATALYSIS; ALPHA-ALLYLATION; ORGANOCATALYSIS; ALKYLATION; ALDEHYDES; ALCOHOLS; STRATEGY;
D O I
10.1002/chem.201404565
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel catalytic enantioselective methodology based on synergistic catalysis is reported. The strategy involves: 1) the metal-Lewis-acid activation of alkylazaarenes, and 2) the secondary-amine activation of enals. Consequently, highly functionalized chiral alkylazaarenes were obtained in good yields and with reasonable stereoselectivity.
引用
收藏
页码:16853 / 16857
页数:5
相关论文
共 50 条
  • [41] Enantioselective α-Vinylation of Aldehydes via the Synergistic Combination of Copper and Amine Catalysis
    Skucas, Eduardas
    MacMillan, David W. C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (22) : 9090 - 9093
  • [42] Regio- and Enantioselective Allylic Cyanomethylation by Synergistic Rhodium and Silane Catalysis
    Sun, Minghe
    Wei, Linsheng
    Li, Changkun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023,
  • [43] Stereocontrol through Synergistic Catalysis in the Enantioselective α-Alkenylation of Aldehyde: A Computational Study
    Patil, Mahendra
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (03): : 1304 - 1311
  • [44] Regio- and Enantioselective Allylic Cyanomethylation by Synergistic Rhodium and Silane Catalysis
    Yang, Min
    Cao, Peng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (04) : 1608 - 1609
  • [45] Regio- and Enantioselective Allylic Cyanomethylation by Synergistic Rhodium and Silane Catalysis
    Sun, Minghe
    Wei, Linsheng
    Li, Changkun
    Journal of the American Chemical Society, 2023,
  • [46] Synergistic Cu-amine catalysis for the enantioselective synthesis of chiral cyclohexenones
    Quintard, A.
    Rodriguez, J.
    CHEMICAL COMMUNICATIONS, 2015, 51 (46) : 9523 - 9526
  • [47] Cooperative Dienamine/Hydrogen-Bonding Catalysis: Enantioselective Formal [2+2] Cycloaddition of Enals with Nitroalkenes
    Talavera, Garazi
    Reyes, Efraim
    Vicario, Jose L.
    Carrillo, Luisa
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (17) : 4104 - 4107
  • [48] Enantioselective β-Protonation of Enals via a Shuttling Strategy
    Chen, Jiean
    Yuan, Pengfei
    Wang, Leming
    Huang, Yong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (20) : 7045 - 7051
  • [50] Dearomative Michael addition involving enals and 2-nitrobenzofurans realized under NHC-catalysis
    Dyguda, Mateusz
    Skrzynska, Anna
    Sieron, Leslaw
    Albrecht, Lukasz
    CHEMICAL COMMUNICATIONS, 2022, 58 (35) : 5367 - 5370