Myoglobin-catalyzed intermolecular carbene N-H insertion with arylamine substrates

被引:144
|
作者
Sreenilayam, Gopeekrishnan [1 ]
Fasan, Rudi [1 ]
机构
[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
关键词
HIGHLY ENANTIOSELECTIVE INSERTION; ALPHA-AMINO-ACIDS; DIAZO-COMPOUNDS; OLEFIN CYCLOPROPANATION; O-H; BONDS; COMPLEXES; ESTERS; ROUTE; DERIVATIVES;
D O I
10.1039/c4cc08753d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Engineered variants of the heme-containing protein myoglobin can efficiently catalyze the insertion of alpha-diazo esters into the N-H bond of arylamines, featuring a combination of high chemoselectivity, elevated turnover numbers, and broad substrate scope.
引用
收藏
页码:1532 / 1534
页数:3
相关论文
共 50 条
  • [1] Myoglobin-catalyzed intermolecular carbene N-H insertion with arylamine substrates (vol 51, pg 1532, 2015)
    Sreenilayam, Gopeekrishnan
    Fasan, Rudi
    CHEMICAL COMMUNICATIONS, 2015, 51 (09) : 1744 - 1744
  • [2] Selective Functionalization of Aliphatic Amines via Myoglobin-Catalyzed Carbene N-H Insertion
    Steck, Viktoria
    Sreenilayam, Gopeekrishnan
    Fasan, Rudi
    SYNLETT, 2020, 31 (03) : 224 - 229
  • [3] Chemoselective N-H insertion catalyzed by a de novo carbene transferase
    Richard, Stenner
    Ross, Anderson John Leslie
    BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY, 2020, 67 (04) : 527 - 535
  • [4] Rhodium(II)-Catalyzed Alkynyl Carbene Insertion into N-H Bonds
    Sharma, Akashdeep
    Vaid, Himani
    Kotwal, Riya
    Mughal, Zuhaib N.
    Gurubrahamam, Ramani
    ORGANIC LETTERS, 2024, 26 (23) : 4887 - 4892
  • [5] Iridium catalyzed acceptor/acceptor carbene insertion into N-H bonds in water
    Ramakrishna, Kankanala
    Sivasankar, Chinnappan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (11) : 2392 - 2396
  • [6] Enantioselective Palladium-Catalyzed Carbene Insertion into the N-H Bonds of Aromatic Heterocycles
    Arredondo, Vanessa
    Hiew, Stanley C.
    Gutman, Eugene S.
    Premachandra, Ilandari Dewage Udara Anulal
    Van Vranken, David L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (15) : 4156 - 4159
  • [7] Copper-Catalyzed Chemoselective Divergent Carbene Insertion into the N-H bonds of Tryptamines
    Kumar, Dharmendra
    Kuram, Malleswara Rao
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (22) : 3935 - 3941
  • [8] Enantioselective palladium-catalyzed insertion of carbene groups into N-H bonds of aromatic heterocyclesα
    Van Vranken, David
    Hiew, Stanley
    Dewage, Udara Ilandari
    Arredondo, Vanessa
    Gutman, Eugene
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [9] Heterogeneous Iridium-Catalyzed Carbene N-H Bond Insertion with α-Alkyl Diazo Esters
    Guo, Ping
    Chen, Yan
    Tao, Lei
    Ji, Shufang
    Zhang, Ruixue
    Zhang, Zedong
    Liang, Xiao
    Wang, Dingsheng
    Li, Yadong
    Zhao, Jie
    ACS CATALYSIS, 2024, 14 (07) : 4690 - 4698
  • [10] Enantioselective carbene insertion into the N-H bond of benzophenone imine
    Yang, Jian
    Ruan, Peiran
    Yang, Wei
    Feng, Xiaoming
    Liu, Xiaohua
    CHEMICAL SCIENCE, 2019, 10 (44) : 10305 - 10309