Enantioselective Synthesis of gem-Diaryl Benzofuran-3(2H)-ones via One-Pot Asymmetric Rhodium/Palladium Relay Catalysis

被引：20
作者：
Zhang, Zong-Feng [1 ,2 ]
Zhu, Dong-Xing [2 ,3 ]
Chen, Wen-Wen [2 ,3 ]
Xu, Bin [1 ]
Xu, Ming-Hua [2 ,3 ]
机构：
[1] Shanghai Univ, Innovat Drug Res Ctr, Dept Chem, Shanghai 200444, Peoples R China
[2] Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China
[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 10期
基金：
美国国家科学基金会;
关键词：
INTRAMOLECULAR STETTER REACTION; C-H FUNCTIONALIZATION; REACTIONS (MC)R-2; DUAL CATALYSIS; QUATERNARY STEREOCENTERS; MULTICATALYTIC REACTIONS; EFFICIENT SYNTHESIS; ALLYLIC ALKYLATION; CHIRAL LIGANDS; REARRANGEMENT;
D O I：
10.1021/acs.orglett.7b01070
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An asymmetric dual-metal relay catalysis strategy that combines Rh/chiral sulfur-olefin-catalyzed enantioselective 1,2-addition with a Pd-catalyzed intramolecular C-O coupling has been developed. The method allows rapid and efficient synthesis of quaternary carbon-containing gem-diaryl benzofuran-3(2H)-ones in good yields in a highly enantioselective manner (up to 99% ee) through a simple one-pot cascade reaction.
引用
收藏
页码：2726 / 2729
页数：4
相关论文
共 56 条
  • [1] Enantioselective Robinson-Type Annulation Reaction Catalyzed by Chiral Phosphoric Acids
    Akiyama, Takahiko
    Katoh, Takuya
    Mori, Keiji
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) : 4226 - 4228
  • [2] Synergistic catalysis: A powerful synthetic strategy for new reaction development
    Allen, Anna E.
    MacMillan, David W. C.
    [J]. CHEMICAL SCIENCE, 2012, 3 (03) : 633 - 658
  • [3] SYNTHESIS OF 2-ARYL-3(2H)-BENZOFURANONES
    BARTON, DHR
    DONNELLY, DMX
    FINET, JP
    GUIRY, PJ
    KIELTY, JM
    [J]. TETRAHEDRON LETTERS, 1990, 31 (46) : 6637 - 6640
  • [4] Highly enantioselective approach to geminal bisphosphonates by organocatalyzed Michael-type addition of β-ketoesters
    Capuzzi, Marinella
    Perdicchia, Dario
    Jorgensen, Karl Anker
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (01) : 128 - 135
  • [5] Asymmetric Organocatalysis Combined with Metal Catalysis: Concept, Proof of Concept, and Beyond
    Chen, Dian-Feng
    Han, Zhi-Yong
    Zhou, Xiao-Le
    Gong, Liu-Zhu
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (08) : 2365 - 2377
  • [6] Relay Rh(II)/Pd(0) Dual Catalysis: Selective Construction of Cyclic All-Quaternary Carbon Centers
    Chen, Zi-Sheng
    Huang, Xiao-Yan
    Gao, Jin-Ming
    Ji, Kegong
    [J]. ORGANIC LETTERS, 2016, 18 (22) : 5876 - 5879
  • [7] Organocatalytic synthesis of spiro compounds via a cascade Michael-Michael-aldol reaction
    Companyo, Xavier
    Zea, Alex
    Alba, Andrea-Nekane R.
    Mazzanti, Andrea
    Moyano, Albert
    Rios, Ramon
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (37) : 6953 - 6955
  • [8] Nickel-Catalyzed Enantioselective C-C Bond Formation through Csp2-O Cleavage in Aryl Esters
    Cornella, Josep
    Jackson, Evan P.
    Martin, Ruben
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) : 4075 - 4078
  • [9] Asymmetric Michael-Aldol Tandem Reaction of 2-Substituted Benzofuran-3-ones and Enones: A Facile Synthesis of Griseofulvin Analogues
    Dong, Nan
    Li, Xin
    Wang, Feng
    Cheng, Jin-Pei
    [J]. ORGANIC LETTERS, 2013, 15 (18) : 4896 - 4899
  • [10] Isolation and Structural Elucidation of Armeniaspirols A-C: Potent Antibiotics against Gram-Positive Pathogens
    Dufour, Cosima
    Wink, Joachim
    Kurz, Michael
    Kogler, Herbert
    Olivan, Helene
    Sable, Serge
    Heyse, Winfried
    Gerlitz, Martin
    Toti, Luigi
    Nusser, Antje
    Rey, Astrid
    Couturier, Cedric
    Bauer, Armin
    Broenstrup, Mark
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (50) : 16123 - 16128
123456