Pd-catalyzed intramolecular C(sp2)–H amination of phenylalanine moieties in dipeptides: synthesis of indoline-2-carboxylate-containing dipeptides

Yong Zheng; Weibin Song; Yefu Zhu; Bole Wei; Lijiang Xuan

doi:10.1039/C8OB00207J

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Pd-catalyzed intramolecular C(sp²)–H amination of phenylalanine moieties in dipeptides: synthesis of indoline-2-carboxylate-containing dipeptides†

Yong Zheng,^a Weibin Song,^a Yefu Zhu,^a Bole Wei^a and Lijiang Xuan

*^a

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* Corresponding authors

^a State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China
E-mail: ljxuan@mail.shcnc.ac.cn

Abstract

A palladium-catalyzed intramolecular C(sp²)–H amination of phenylalanine moieties in dipeptides is described. By this protocol, a series of indoline-2-carboxylate-containing dipeptides were synthesized from dipeptides. The N-protected amino acid moiety within the peptide is used as an intrinsic bidentate directing group. This intramolecular C–H amination reaction provides an appealing strategy for the post-synthetic modification of peptides.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C8OB00207J
Article type: Communication
Submitted: 25 Jan 2018
Accepted: 13 Mar 2018
First published: 22 Mar 2018

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Org. Biomol. Chem., 2018,16, 2402-2405

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Pd-catalyzed intramolecular C(sp²)–H amination of phenylalanine moieties in dipeptides: synthesis of indoline-2-carboxylate-containing dipeptides

Y. Zheng, W. Song, Y. Zhu, B. Wei and L. Xuan, Org. Biomol. Chem., 2018, 16, 2402 DOI: 10.1039/C8OB00207J

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Organic & Biomolecular Chemistry