Gold/BrOnsted Acid Relay Catalysis for Enantioselective Construction of Spirocyclic Diketones

被引:53
|
作者
Qian, Deyun [1 ]
Zhang, Junliang [1 ]
机构
[1] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
关键词
asymmetric catalysis; gold; quaternary center; relay catalysis; spirocycles; STEREOSELECTIVE CONSTRUCTION; GOLD; METAL; FLUORINE; LIGANDS;
D O I
10.1002/chem.201301208
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Golden opportunities: A redox-, atom-, and step-economical asymmetric cascade reaction for the synthesis of chiral spirocyclic architectures with two contiguous stereocenters in high yields and excellent enantioselectivities by using a gold/chiral Brønsted acid relay catalysis system is described (see scheme). The results suggest that the chiral Brønsted acid rather than the chiral gold phosphate complex serves as the real catalyst of the enantiodetermining step. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:6984 / 6988
页数:5
相关论文
共 50 条
  • [1] Enantioselective Construction of Functionalized Tetrahydrocarbazoles Enabled by Asymmetric Relay Catalysis of Gold Complex and Chiral Bronsted Acid
    Zhao, Feng
    Li, Nan
    Zhu, Yi-Fan
    Han, Zhi-Yong
    ORGANIC LETTERS, 2016, 18 (07) : 1506 - 1509
  • [2] Relay Iron/Chiral Bronsted Acid Catalysis: Enantioselective Hydrogenation of Benzoxazinones
    Lu, Liang-Qiu
    Li, Yuehui
    Junge, Kathrin
    Beller, Matthias
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (07) : 2763 - 2768
  • [3] Enantioselective Hydroaminomethylation of Olefins Enabled by Rh/Bronsted Acid Relay Catalysis
    Meng, Jing
    Li, Xing-Han
    Han, Zhi-Yong
    ORGANIC LETTERS, 2017, 19 (05) : 1076 - 1079
  • [4] Isothiourea and Bronsted Acid Cooperative Catalysis: Enantioselective Construction of Dihydropyridinones
    Zhang, Yu-Chen
    Geng, Rui-Long
    Song, Jin
    Gong, Liu-Zhu
    ORGANIC LETTERS, 2020, 22 (06) : 2261 - 2265
  • [5] Enantioselective α-Carbonylative Arylation for Facile Construction of Chiral Spirocyclic β,β′-Diketones
    Wu, Ting
    Zhou, Qinghai
    Tang, Wenjun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (18) : 9978 - 9983
  • [6] Hybrid Gold/Chiral Bronsted Acid Relay Catalysis Allows an Enantioselective Synthesis of (-)-5-epi-Eupomatilone-6
    Wu, Xiang
    Li, Ming-Li
    Wang, Pu-sheng
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (01): : 419 - 425
  • [7] Enantioselective heterogeneous Bronsted acid catalysis
    Mutyala, Anil Kumar
    Patil, Nitin T.
    ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (05): : 582 - 586
  • [8] Visible-Light Induction/Bronsted Acid Catalysis in Relay for the Enantioselective Synthesis of Tetrahydroquinolines
    Xiong, Wenhui
    Li, Shan
    Fu, Bo
    Wang, Jinping
    Wang, Qiu-An
    Yang, Wen
    ORGANIC LETTERS, 2019, 21 (11) : 4173 - 4176
  • [9] When gold meets chiral Bronsted acid catalysts: extending the boundaries of enantioselective gold catalysis
    Inamdar, Suleman M.
    Konala, Ashok
    Patil, Nitin T.
    CHEMICAL COMMUNICATIONS, 2014, 50 (96) : 15124 - 15135
  • [10] Enantioselective Bronsted acid catalysis with chiral cyclopentadienes
    Gheewala, Chirag
    Collins, Bridget
    Lambert, Tristan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253