A general and practical palladium-catalyzed monoarylation of β-methyl C(sp3)-H of alanine

被引：76

作者：

Chen, Kai ^{[1
]}

Zhang, Shuo-Qing ^{[1
]}

Xu, Jing-Wen ^{[1
]}

Hu, Fang ^{[1
]}

Shi, Bing-Feng ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 90期

关键词：

C-H BONDS; CARBON-HYDROGEN BONDS; ALPHA-AMINO-ACIDS; UNACTIVATED C(SP(3))-H; DIRECTING GROUP; STEREOSELECTIVE-SYNTHESIS; DIRECT FUNCTIONALIZATION; ASYMMETRIC-SYNTHESIS; BIDENTATE AUXILIARY; COUPLING REACTIONS;

D O I：

10.1039/c4cc06652a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A palladium-catalyzed monoarylation of beta-methyl C(sp(3))-H of an alanine derivative with aryl iodides using an 8-aminoquinoline auxiliary is described. The reaction is highly efficient, scalable and compatible with a variety of functional groups with complete retention of chirality, providing a general and practical access to various beta-aryl-alpha-amino acids. The synthetic potential of this protocol is further demonstrated in the sequential synthesis of diverse beta-branched alpha-amino acids.

引用

页码：13924 / 13927

页数：4

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