Blue light-promoted N-H insertion of amides, isatins, sulfonamides and imides into aryldiazoacetates: Synthesis of unnatural α-aryl amino acid derivatives

被引：27

作者：

Okada Jr, Celso Y. ^{[1
]}

dos Santos, Caio Y. ^{[1
]}

Jurberg, Igor D. ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Chem, BR-13083862 Campinas, SP, Brazil

来源：

TETRAHEDRON | 2020年 / 76卷 / 51期

基金：

巴西圣保罗研究基金会;

关键词：

Photochemistry; Visible light; Carbenes; N-H insertion; Amides; PHASE-TRANSFER CATALYSIS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; GENERAL-APPROACH; KETO ACIDS; CONVERSION; ALKYLATION; ARYLGLYCINES; AMINATION; GLYCINE;

D O I：

10.1016/j.tet.2020.131316

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A photochemical protocol using blue light allows the N-H insertion of amides, isatins, sulfonamides and imides into aryldiazoacetates to afford the corresponding alpha-amino esters. This method is experimentally simple, inexpensive and tolerates numerous functional groups, thus allowing the straightforward preparation of a variety of alpha-aryl amino acid derivatives in good yields. (C) 2020 Published by Elsevier Ltd.

引用

页数：10

共 20 条

[1] Blue light-promoted N-H insertion of amides, isatins, sulfonamides and imides into arylidiazoacetates: Synthesis of unnatural α-aryl amino acid derivatives (vol 76, 131316, 2020)
Okada Jr, Celso Y.
dos Santos, Caio Y.
Jurberg, Igor D.
TETRAHEDRON, 2024, 167
[2] Blue Light-Promoted N-H Insertion of Carbazoles, Pyrazoles and 1,2,3-Triazoles into Aryldiazoacetates
Stivanin, Mateus L.
Fernandes, Alessandra A. G.
da Silva, Amanda F.
Okada Jr, Celso Y.
Jurberg, Igor D.
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (05) : 1106 - 1111
[3] N-H insertion reactions of boc-amino acid amides: Solution- and solid-phase synthesis of pyrazinones and pyrazines
Matsushita, H
Lee, SH
Yoshida, K
Clapham, B
Koch, G
Zimmermann, J
Janda, KD
ORGANIC LETTERS, 2004, 6 (24) : 4627 - 4629
[4] Enantioselective Synthesis of Unnatural Carbamate-Protected α-Alkyl Amino Esters via N-H Bond Insertion Reactions
Li, You
Su, Yu-Xuan
Zhao, Yu-Tao
Liu, Lu
Li, Mao-Lin
Zhu, Shou-Fei
ACS CATALYSIS, 2022, 12 (21): : 13143 - 13148
[5] 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)
[6] Visible-Light-Induced Insertion of Siloxycarbene into Amide N-H Bonds: Synthesis of Carbinolamides from Acylsilanes and Amides
Dharavath, Praveen
Vaggu, Raju
Manda, Rajesh
Gree, Rene
Das, Saibal
JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (04): : 1727 - 1732
[7] Enantioselective hydrogenation of α-aminomethylacrylates containing a free N-H group for the synthesis of β-amino acid derivatives
Qiu, Liqin
Prashad, Mahavir
Hu, Bin
Prasad, Kapa
Repic, Oljan
Blacklock, Thomas J.
Kwong, Fuk Yee
Kok, Stanton H. L.
Lee, Hang Wai
Chan, Albert S. C.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (43) : 16787 - 16792
[8] N-H insertion reactions of rhodium carbenoids .1. Preparation of alpha-amino acid and alpha-aminophosphonic acid derivatives
Aller, E
Buck, RT
Drysdale, MJ
Ferris, L
Haigh, D
Moody, CJ
Pearson, ND
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JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (24): : 2879 - 2884
[9] Synthesis of Unnatural Amino Acid Derivatives by Visible-Light-Catalyzed Decarboxylative Alkylation of N-Aromatic Glyoxylimines
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Zhang Xuming
Sun Hanyang
Leng Jinyao
Li Yaming
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (12) : 4284 - 4293
[10] Visible-light-mediated catalytic asymmetric synthesis of a-amino esters via free carbene insertion into N-H bond
Zhou, Ying
Zhang, Yan
Yu, Canghai
Yue, Xin
Jiang, Feng
Guo, Wengang
TETRAHEDRON LETTERS, 2023, 122

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