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

被引：145
|
作者：
Sreenilayam, Gopeekrishnan [1 ]
Fasan, Rudi [1 ]
机构：
[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
来源：
CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 08期
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
  • [21] Enantioselective insertion of carbenoids into N-H bonds catalyzed by chiral bicyclobisoxazoline copper(I) complexes
    Le Maux, Paul
    Simonneaux, Gerard
    TETRAHEDRON, 2015, 71 (49) : 9333 - 9338
  • [22] Cinchona alkaloids induce asymmetry in the insertion reaction of thermally generated carbenes into N-H bonds
    Saito, Hiroaki
    Morita, Daisuke
    Uchiyama, Taketo
    Miyake, Muneharu
    Miyairi, Shinichi
    TETRAHEDRON LETTERS, 2012, 53 (49) : 6662 - 6664
  • [23] Cytochrome P450-catalyzed insertion of carbenoids into N-H bonds
    Wang, Z. Jane
    Peck, Nicole E.
    Renata, Hans
    Arnold, Frances H.
    CHEMICAL SCIENCE, 2014, 5 (02) : 598 - 601
  • [24] Enantioselective synthesis of chiral amides by carbene insertion into amide N-H bond
    Zhang, Xuan-Ge
    Yang, Zhi-Chun
    Pan, Jia-Bin
    Liu, Xiao-Hua
    Zhou, Qi-Lin
    NATURE COMMUNICATIONS, 2024, 15 (01)
  • [25] Mechanistic investigations on asymmetric N-H insertion of amines catalyzed by palladium-chiral guanidine complex
    Li, Jing
    Su, Zhishan
    Wang, Junming
    Hu, Changwei
    JOURNAL OF CATALYSIS, 2018, 364 : 426 - 436
  • [26] Chemoselective Cyclopropanation over Carbene Y-H Insertion Catalyzed by an Engineered Carbene Transferase
    Moore, Eric J.
    Steck, Viktoria
    Bajaj, Priyanka
    Fasan, Rudi
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (14) : 7480 - 7490
  • [27] Preparation of Axially Chiral 2,2′-Biimidazole Ligands through Remote Chirality Delivery and Their Application in Asymmetric Carbene Insertion into N-H of Carbazoles
    Shen, Hong-Qiang
    Wu, Bo
    Xie, Huan-Ping
    Zhou, Yong-Gui
    ORGANIC LETTERS, 2019, 21 (08) : 2712 - 2717
  • [28] Hemin-Catalyzed, Cyclodextrin-Assisted Insertion of Carbenoids into N-H Bonds
    Xu, Xiaofei
    Li, Chang
    Tao, Zhihao
    Pan, Yuanjiang
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (14-15) : 3341 - 3345
  • [29] Bismuth-catalyzed arylation of ethyl glyoxylate with aniline via N-H insertion
    Bin Riyaz, Mohd Aamir
    Premkumar, G.
    Swu, Toka
    MOLECULAR DIVERSITY, 2023, 27 (01) : 167 - 175
  • [30] Enantioselective Copper-Catalyzed Intramolecular N-H Bond Insertion: Synthesis of Chiral 2-Carboxytetrahydroquinolines
    Song, Xiao-Guang
    Ren, Yuan-Yuan
    Zhu, Shou-Fei
    Zhou, Qi-Lin
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (15) : 2366 - 2370
12345