Site-specific indolation of proline-based peptides via copper(II)-catalyzed oxidative coupling of tertiary amine N-oxides

被引：13

作者：

Wu, Xiaowei ^{[1
]}

Zhang, Dengyou ^{[1
]}

Zhou, Shengbin ^{[1
]}

Gao, Feng ^{[1
]}

Liu, Hong ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 63期

基金：

中国国家自然科学基金;

关键词：

C-H BONDS; TERMINAL FUNCTIONALIZATION; GLYCINE DERIVATIVES; AFFINITY; COMPLEX; ALKYNES;

D O I：

10.1039/c5cc03706a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first site-specific and purely chemical method for modifying proline-based peptides was developed via a convenient, copper-catalyzed oxidative coupling of tertiary amine N-oxides with indoles. This novel approach features high regioselectivity and diastereo-selectivity, mild conditions, and compatibility with various functional groups. In addition, a simplified process was realized in one pot and two steps via in situ oxidative coupling of tertiary amine and indoles.

引用

页码：12571 / 12573

页数：3

共 6 条

[1] Propargylamine Synthesis by Copper-Catalyzed Oxidative Coupling of Alkynes and Tertiary Amine N-Oxides
Xu, Zhanwei
Yu, Xiaoqiang
Feng, Xiujuan
Bao, Ming
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (16): : 6901 - 6905
[2] Copper(II) catalyzed reaction of gaseous alkanes with amine N-oxides
Taniguchi, Y
Kitamura, T
Fujiwara, Y
Horie, S
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CATALYSIS TODAY, 1997, 36 (01) : 85 - 89
[3] Synthesis of 2-Pyridinemethyl Ester Derivatives from Aldehydes and 2-Alkylheterocycle N-Oxides via Copper-Catalyzed Tandem Oxidative Coupling-Rearrangement
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ORGANIC LETTERS, 2017, 19 (24) : 6720 - 6723
[4] Amine Oxidative N-Dealkylation via Cupric Hydroperoxide Cu-OOH Homolytic Cleavage Followed by Site-Specific Fenton Chemistry
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Ginsbach, Jake W.
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Peterson, Ryan L.
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (08) : 2867 - 2874
[5] Formation of the Tertiary Sulfonamide C(sp3)-N Bond Using Alkyl Boronic Ester via Intramolecular and Intermolecular Copper-Catalyzed Oxidative Cross-Coupling
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Lee, Hong Geun
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 17380 - 17394
[6] Copper(II)-Catalyzed Oxidative Coupling of Anilines, Methyl Arenes, and TMSN3 via C(sp3/sp2)-H Functionalization and C-N Bond Formation
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Satheesh, Vanaparthi
Kumar, Sundaravel Vivek
Punniyamurthy, Tharmalingam
ORGANIC LETTERS, 2017, 19 (24) : 6554 - 6557

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