Arylglycine-derivative synthesis via oxidative sp3 C-H functionalization of α-amino esters

被引：21

作者：

Xu, Zhanwei ^{[1
]}

Yu, Xiaoqiang ^{[1
]}

Feng, Xiujuan ^{[1
]}

Bao, Ming ^{[1
]}

机构：

[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116023, Peoples R China

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 8卷

基金：

中国国家自然科学基金;

关键词：

alpha-amino ester; arylglycine; C-H functionalization; oxidation; synthesis; ASYMMETRIC-SYNTHESIS; ACIDS;

D O I：

10.3762/bjoc.8.178

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the synthesis of arylglycine derivatives is described. The oxidative coupling reactions of naphthols and phenols with alpha-amino esters proceeded smoothly in the presence of meta-chloroperoxybenzoic acid as an oxidant under ambient conditions, to produce arylglycine derivatives in satisfactory yields.

引用

页码：1564 / 1568

页数：5

共 21 条

[1] Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters
Beenen, Melissa A.
Weix, Daniel J.
Ellman, Jonathan A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (19) : 6304 - 6305
[2] Synthesis of 1-hydroxypyrazole glycine derivatives
Calí, P
Begtrup, M
[J]. TETRAHEDRON, 2002, 58 (08) : 1595 - 1605
[3] Boronic Acids and Esters in the Petasis-Borono Mannich Multicomponent Reaction
Candeias, Nuno R.
Montalbano, Francesco
Cal, Pedro M. S. D.
Gois, Pedro M. P.
[J]. CHEMICAL REVIEWS, 2010, 110 (10) : 6169 - 6193
[4] A Copper-Catalyzed Petasis Reaction for the Synthesis of Tertiary Amines and Amino Esters
Frauenlob, Robin
Garcia, Carlos
Bradshaw, Gary A.
Burke, Helen M.
Bergin, Enda
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (09) : 4445 - 4449
[5] Grierson D., 1990, ORG REACT, V39, P85, DOI [10.1002/0471264180.or039.02, DOI 10.1002/0471264180.OR039.02]
[6] Gröger H, 2001, ADV SYNTH CATAL, V343, P547, DOI 10.1002/1615-4169(200108)343:6/7<547::AID-ADSC547>3.0.CO
[7] 2-A
[8] Grumbach HJ, 1999, SYNTHESIS-STUTTGART, P1027
[9] One-pot, regioselective synthesis of substituted arylglycines for kinetic resolution by penicillin G acylase
Grundmann, Peter
Fessner, Wolf-Dieter
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (11-12) : 1729 - 1735
[10] A modified Mannich-type reaction catalyzed by VO(acac)2
Hwang, DR
Uang, BJ
[J]. ORGANIC LETTERS, 2002, 4 (03) : 463 - 466

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