Palladium-catalyzed β-C(sp(3))-H arylation of phthaloyl alanine with hindered aryl iodides: synthesis of complex β-aryl α-amino acids

Organic & Biomolecular Chemistry
Xuekai ZhangGong Chen

Abstract

An efficient protocol for palladium-catalyzed β-C(sp(3))-H arylation of aliphatic carboxamides equipped with a 2-(2-pyridyl) ethylamine (PE) auxiliary was developed. The PE auxiliary is uniquely effective at facilitating the arylation of primary C(sp(3))-H bonds with sterically hindered aryl iodides. A variety of aryl iodides bearing alkoxyl, carbonyl, nitro and halogen groups on the ortho position can react with the PE-coupled phthaloyl alanine substrate in moderate to excellent yield. These reactions offer a useful solution for preparing complex β-aryl α-amino acid products from readily accessible starting materials.

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Citations

Feb 19, 2016·Organic & Biomolecular Chemistry·Matthew B Calvert, Jonathan Sperry
Feb 10, 2018·Angewandte Chemie·Ming ChenGuangbin Dong
Jul 24, 2018·Chemical Society Reviews·Carlo SambiagioMichael Schnürch
Apr 23, 2020·The Journal of Organic Chemistry·Pratibha Chand-ThakuriMichael C Young
Jun 28, 2019·The Journal of Organic Chemistry·Zhiguo ZhangGong Chen
Jul 13, 2017·Chemical Reviews·Jian HeJin-Quan Yu

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