Biomimetic Asymmetric Hydrogenation: In Situ Regenerable Hantzsch Esters for Asymmetric Hydrogenation of Benzoxazinones

被引：168
作者：
Chen, Qing-An [1 ]
Chen, Mu-Wang [1 ]
Yu, Chang-Bin [1 ]
Shi, Lei [1 ]
Wang, Duo-Sheng [1 ]
Yang, Yan [1 ]
Zhou, Yong-Gui [1 ]
机构：
[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 41期
基金：
中国国家自然科学基金;
关键词：
ENANTIOSELECTIVE TRANSFER HYDROGENATION; ORGANOCATALYTIC TRANSFER HYDROGENATION; BRONSTED ACID CATALYSIS; ALPHA-IMINO ESTERS; CHIRAL PHOSPHORIC-ACIDS; TRANSITION-METAL; COOPERATIVE CATALYSIS; REDUCTIVE AMINATION; RELAY CATALYSIS; IRIDIUM;
D O I：
10.1021/ja208073w
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A catalytic amount of Hantzsch ester that could be regenerated in situ by Ru complexes under hydrogen gas has been employed in the biomimetic asymmetric hydrogenation of benzoxazinones with up to 99% ee in the presence of chiral phosphoric acid. The use of hydrogen gas as a reductant for the regeneration of Hantzsch esters makes this hydrogenation an ideal atom economic process.
引用
收藏
页码：16432 / 16435
页数：4
相关论文
共 96 条
  • [1] Stronger bronsted acids
    Akiyama, Takahiko
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5744 - 5758
  • [2] Recent progress in chiral Bronsted acid catalysis
    Akiyama, Takahiko
    Itoh, Junji
    Fuchibe, Kohei
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) : 999 - 1010
  • [3] Anderson P. G, 2008, MODERN REDUCTION MET
  • [4] [Anonymous], 2007, The Handbook of Homogeneous Hydrogenation
  • [5] New Trends in the Recycling of NAD(P)H for the Design of Sustainable Asymmetric Reductions Catalyzed by Dehydrogenases
    Berenguer-Murcia, Angel
    Fernandez-Lafuente, Roberto
    [J]. CURRENT ORGANIC CHEMISTRY, 2010, 14 (10) : 1000 - 1021
  • [6] Enantioselective Intramolecular Aza-Michael Additions of Indoles Catalyzed by Chiral Phosphoric Acids
    Cai, Quan
    Zheng, Chao
    You, Shu-Li
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (46) : 8666 - 8669
  • [7] Asymmetric Construction of Polycyclic Indoles through Olefin Cross-Metathesis/Intramolecular Friedel-Crafts Alkylation under Sequential Catalysis
    Cai, Quan
    Zhao, Zhuo-An
    You, Shu-Li
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (40) : 7428 - 7431
  • [8] Convergent Asymmetric Disproportionation Reactions: Metal/Bronsted Acid Relay Catalysis for Enantioselective Reduction of Quinoxalines
    Chen, Qing-An
    Wang, Duo-Sheng
    Zhou, Yong-Gui
    Duan, Ying
    Fan, Hong-Jun
    Yang, Yan
    Zhang, Zhang
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (16) : 6126 - 6129
  • [9] Asymmetric organocatalytic reductions mediated by dihydropyridines
    Connon, Stephen J.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (21) : 3407 - 3417
  • [10] Asymmetric hydrogenation of aromatic compounds
    Glorius, F
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (23) : 4171 - 4175
12345678910