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
收藏
页码：13924 / 13927
页数：4
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