Sulfonamide-Promoted Palladium(II)-Catalyzed Alkylation of Unactivated Methylene C(sp3)-H Bonds with Alkyl Iodides

被引：128
|
作者：
Chen, Kai [1 ]
Shi, Bing-Feng [1 ]
机构：
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 44期
关键词：
alkylation; C-H activation; palladium; amino acids; synthetic methods; C-H BONDS; PALLADIUM-CATALYZED ALKYLATION; CROSS-COUPLING REACTIONS; STEREOSELECTIVE-SYNTHESIS; DIRECTING GROUP; AMINO-ACIDS; ARYLATION; FUNCTIONALIZATION; HALIDES; SP(2);
D O I：
10.1002/anie.201407848
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The alkylation of unactivated beta-methylene C(sp(3))-H bonds of alpha-amino acid substrates with a broad range of alkyl iodides using Pd(OAc)(2) as the catalyst is described. The addition of NaOCN and 4-Cl-C6H4SO2NH2 was found to be crucial for the success of this transformation. The reaction is compatible with a diverse array of functional groups and proceeds with high diastereoselectivity. Furthermore, various beta,beta-hetero-dialkyl-and beta-alkyl-beta-aryl-alpha-amino acids were prepared by sequential C(sp(3))-H functionalization of an alanine-derived substrate, thus providing a versatile strategy for the stereoselective synthesis of unnatural beta-disubstituted alpha-amino acids.
引用
收藏
页码：11950 / 11954
页数：5
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