Synthesis of enantiomerically-enriched N-aryl amino-amides via a Jocic-type reaction

被引：6

作者：

Hobson, Christian ^{[1
]}

Perryman, Michael S. ^{[1
]}

Kirby, Gavin ^{[1
]}

Clarkson, Guy J. ^{[1
]}

Fox, David J. ^{[1
]}

机构：

[1] Univ Warwick, Dept Chem, Gibbet Hill Rd, Coventry CV4 7AL, W Midlands, England

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 44期

关键词：

Jocic reaction; N-Aryl amino-amides; Enantiomerically-enriched; ASYMMETRIC TRANSFER HYDROGENATION; COREY-LINK REACTION; CATALYZED COUPLING REACTION; C-N; ENANTIOSPECIFIC SYNTHESIS; PRIMARY ALCOHOLS; ENANTIOSELECTIVE SYNTHESIS; ALPHA-AMINOESTERS; ALIPHATIC-AMINES; (-)-INDOLACTAM V;

D O I：

10.1016/j.tetlet.2018.09.046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically-enriched secondary trichloromethyl-alcohols react with aryl amines to give enantiomerically-enriched alpha-N-arylamino-acid derivatives. The intermediate acid chlorides can react in situ with aryl or, regioselectively, with alkyl amines to give aryl or alkyl alpha-N-arylamino amides. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：3965 / 3968

页数：4

共 3 条

[1] Synthesis of 1-and 4-substituted piperazin-2-ones via Jocic-type reactions with N-substituted diamines
Perryman, Michael S.
Earl, Matthew W. M.
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Clarkson, Guy J.
Fox, David J.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (08) : 2360 - 2365
[2] Design of Photoredox-Catalyzed Giese-Type Reaction for the Synthesis of Chiral Quaternary α-Aryl Amino Acid Derivatives via Clayden Rearrangement
Ji, Peng
Chen, Jing
Meng, Xiang
Gao, Feng
Dong, Yue
Xu, Hang
Wang, Wei
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (21): : 14706 - 14714
[3] Dual C-H functionalization of N-aryl tetrahydroisoquinolines: a highly diastereoselective synthesis of dibenzo[a,f]quinolizines via visible-light induced oxidation and inverse electron-demand aza-Diels-Alder reaction
Xu, Guo-Qiang
Li, Chen-Guang
Liu, Ming-Qian
Cao, Jian
Luo, Yong-Chun
Xu, Peng-Fei
CHEMICAL COMMUNICATIONS, 2016, 52 (06) : 1190 - 1193

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