Enantioselective oxidative functionalization of the Csp3-H bond adjacent to a nitrogen atom for rapid access to β-hydroxyl-α-amino acid derivatives

Lin Qiu; Xin Guo; Yu Qian; Changcheng Jing; Chaoqun Ma; Shunying Liu; Wenhao Hu

doi:10.1039/c6cc04710f

Enantioselective oxidative functionalization of the C_sp³-H bond adjacent to a nitrogen atom for rapid access to β-hydroxyl-α-amino acid derivatives

Chem Commun (Camb). 2016 Sep 27;52(79):11831-11833. doi: 10.1039/c6cc04710f.

Authors

Lin Qiu¹, Xin Guo², Yu Qian², Changcheng Jing², Chaoqun Ma², Shunying Liu², Wenhao Hu²

Affiliations

¹ Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Rd., Shanghai, 200062, China. syliu@sist.ecnu.edu.cn whu@chem.ecnu.edu.cn and Xiangya International Academy of Translational Medicine, Central South University, 172 Tongzipo Rd., Changsha, Hunan Province 410013, China.
² Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Rd., Shanghai, 200062, China. syliu@sist.ecnu.edu.cn whu@chem.ecnu.edu.cn.

PMID: 27709161
DOI: 10.1039/c6cc04710f

Abstract

Highly chemoselective and enantioselective one-pot reactions involved in the oxidative functionalization of C_sp³-H bonds adjacent to nitrogen atoms in N-aryl glycine esters were developed. The method provided rapid access to a variety of highly functionalized β-hydroxyl-α-amino acid derivatives from simple starting materials under mild conditions.