Enantioselective Vinylogous Allylic Alkylation of Coumarins with Morita-Baylis-Hillman Carbonates Catalyzed by Chiral Phosphine-Amide

被引：3
|
作者：
Cheng Chun-Xia
Wu Lu-Ping
Sha Feng
Wu Xin-Yan [1 ]
机构：
[1] East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Shanghai 200237, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 43卷 / 09期
基金：
上海市自然科学基金;
关键词：
allylic alkylation; asymmetric catalysis; chiral phosphine; organocatalysis; vinylogous reaction; ORGANOCATALYSTS; DERIVATIVES; SCAFFOLD;
D O I：
10.6023/cjoc202303035
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An organocatalytic enantioselective direct vinylogous allylic alkylation between coumarins and racemic Morita-Baylis-Hillman carbonates has been developed. With 10 similar to 15 mol% a chiral cyclohexane-based phosphine-amide C10, a wide range of densely functionalized coumarin derivatives have been achieved in 87%similar to 99% yields and up to 98% ee.
引用
收藏
页码：3188 / 3195
页数：8
相关论文
共 45 条
  • [1] Enolizable Alkylidene Heterocyclic and Carbocyclic Carbonyl Systems: Valuable Vinylogous Donor Substrates in Synthesis
    Battistini, Lucia
    Curti, Claudio
    Rassu, Gloria
    Sartori, Andrea
    Zanardi, Franca
    [J]. SYNTHESIS-STUTTGART, 2017, 49 (11): : 2297 - 2336
  • [2] Dramatic rate acceleration of the Baylis-Hillman reaction in homogeneous medium in the presence of water
    Cai, JX
    Zhou, ZH
    Zhao, GF
    Tang, CC
    [J]. ORGANIC LETTERS, 2002, 4 (26) : 4723 - 4725
  • [3] The Vinylogous Aldol and Related Addition Reactions: Ten Years of Progress
    Casiraghi, Giovanni
    Battistini, Lucia
    Curti, Claudio
    Rassu, Gloria
    Zanardi, Franca
    [J]. CHEMICAL REVIEWS, 2011, 111 (05) : 3076 - 3154
  • [4] Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis
    Cordes, Martin
    Kalesse, Markus
    [J]. MOLECULES, 2019, 24 (17):
  • [5] Direct Asymmetric Allylic Alkylation of Butenolides with Morita-Baylis-Hillman Carbonates
    Cui, Hai-Lei
    Huang, Ji-Rong
    Lei, Jie
    Wang, Zhao-Feng
    Chen, Shi
    Wu, Li
    Chen, Ying-Chun
    [J]. ORGANIC LETTERS, 2010, 12 (04) : 720 - 723
  • [6] Dual Organocatalysis: Asymmetric Allylic-Allylic Alkylation of α,α-Dicyanoalkenes and Morita-Baylis-Hillman Carbonates
    Cui, Hai-Lei
    Peng, Jing
    Feng, Xin
    Du, Wei
    Jiang, Kun
    Chen, Ying-Chun
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (07) : 1574 - 1577
  • [7] New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems
    Curti, Claudio
    Battistini, Lucia
    Sartori, Andrea
    Zanardi, Franca
    [J]. CHEMICAL REVIEWS, 2020, 120 (05) : 2448 - 2612
  • [8] Vinylogous and Arylogous Stereoselective Base-Promoted Phase-Transfer Catalysis
    D'Amato, Assunta
    Della Sala, Giorgio
    [J]. CATALYSTS, 2021, 11 (12)
  • [9] Palladium-Catalyzed Stereospecific C-Glycosylation of Glycals with Vinylogous Acceptors
    Dai, Yuanwei
    Tian, Baotong
    Chen, Huan
    Zhang, Qiang
    [J]. ACS CATALYSIS, 2019, 9 (04): : 2909 - 2915
  • [10] Coumarins as privileged scaffold for anti-inflammatory drug development
    Grover, Jagdeep
    Jachak, Sanjay M.
    [J]. RSC ADVANCES, 2015, 5 (49) : 38892 - 38905
12345