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

页码：1532 / 1534

页数：3

共 50 条

[41] Synthesis of Tetrahydropyridazines by a Metal-Carbene-Directed Enantioselective Vinylogous N-H Insertion/Lewis Acid-Catalyzed Diastereoselective Mannich Addition
Xu, Xinfang
Zavalij, Peter Y.
Doyle, Michael P.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (39) : 9829 - 9833
[42] O-H insertion and tandem N-H insertion/cyclization reactions using an iron porphyrin as catalyst with diazo compounds as carbene sources
Mbuvi, Harun M.
Klobukowski, Erik R.
Roberts, Gina M.
Woo, L. Keith
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2010, 14 (03) : 284 - 292
[43] Asymmetric N-H Insertion Reaction of α-Diazoesters and Carbamates Co-catalyzed by Dirhodium Acetate, Sufonic Acid and Chiral Sulfonamide Urea
Ni, Yi
Guo, Xin
Hu, Wenhao
Liu, Shunying
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (01) : 107 - 111
[44] Ethyl cellulose derived porous iron@N-doped carbon material for N-H carbene insertion reaction
Lin, Yamei
Wang, Fei
Lu, Guo-Ping
Zhang, Xing
TETRAHEDRON, 2021, 98
[45] Maghemite Supported Copper Oxide Nanocatalyst for the N-H Insertion Reaction with Ethyl Diazoacetate
Ebrahimi, Ali
Heydari, Akbar
Esrafili, Ali
CATALYSIS LETTERS, 2014, 144 (12) : 2204 - 2209
[46] Preparation of N-Acetyl-2-arylglycin Esters by N-H Insertion Reaction of Aryldiazoacetates with Acetamide
Huang, Dan
Jiang, Guo-Ming
Chen, Hong-Xia
Gao, Wen-Dong
SYNTHETIC COMMUNICATIONS, 2010, 40 (02) : 229 - 234
[47] Mechanistic Insight into Asymmetric N-H Insertion Cooperatively Catalyzed by a Dirhodium Compound and a Spiro Chiral Phosphoric Acid
Wang, Xu-Chao
Song, Xian-Shuang
Guo, Li-Ping
Qu, Deyu
Xie, Zhi-Zhong
Verpoort, Francis
Cao, Jun
ORGANOMETALLICS, 2014, 33 (15) : 4042 - 4050
[48] Carbene insertion to N-H bonds of 2-aminothiazole and 2-amino-1,3,4-thiadiazole derivatives catalyzed by iron phthalocyanine
Cailler, Lucie P.
Martynov, Alexander G.
Gorbunova, Yulia G.
Tsivadze, Asian Yu
Sorokin, Alexander B.
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2019, 23 (4-5) : 497 - 506
[49] Heterogeneous Rhodium Single-Atom-Site Catalyst Enables Chemoselective Carbene N-H Bond Insertion
Chen, Yuanjun
Zhang, Ruixue
Chen, Zhiwen
Liao, Jiangwen
Song, Xuedong
Liang, Xiao
Wang, Yu
Dong, Juncai
Singh, Chandra Veer
Wang, Dingsheng
Li, Yadong
Toste, F. Dean
Zhao, Jie
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (15) : 10847 - 10856
[50] Catalytic N-H Insertion Reactions with α-Diazoacetates: An Efficient Method for Enantioselective Amino Acid Synthesis
Su, Yu-Xuan
Huang, Ming-Yao
Zhu, Shou-Fei
CHEMCATCHEM, 2023, 15 (15)

← 1 2 3 4 5 →