Expedient synthesis of chiral α-amino acids through nickel-catalyzed reductive cross-coupling

Xi Lu; Jun Yi; Zhen-Qi Zhang; Jian-Jun Dai; Jing-Hui Liu; Bin Xiao; Yao Fu; Lei Liu

doi:10.1002/chem.201405296

Expedient synthesis of chiral α-amino acids through nickel-catalyzed reductive cross-coupling

Chemistry. 2014 Nov 17;20(47):15339-43. doi: 10.1002/chem.201405296. Epub 2014 Oct 14.

Authors

Xi Lu¹, Jun Yi, Zhen-Qi Zhang, Jian-Jun Dai, Jing-Hui Liu, Bin Xiao, Yao Fu, Lei Liu

Affiliation

¹ Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China); State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000 (China); Department of Chemistry, Tsinghua University, Beijing 100084 (China).

PMID: 25314635
DOI: 10.1002/chem.201405296

Abstract

A novel method for the synthesis of non-natural L- and D-amino acids by a Ni-catalyzed reductive cross-coupling reaction is described. This strategy enables the racemization-free cross-coupling of serine/homoserine- derived iodides with aryl/acyl/alkyl halides. It provides convenient access to varieties of enantiopure and functionalized amino acids, which are important building blocks in bioactive compounds and pharmaceuticals.

Keywords: CC bond formation; amino acids; catalysis; nickel; reductive cross-coupling.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemical synthesis
Amino Acids / chemistry*
Catalysis
Crystallography, X-Ray
Halogens / chemistry
Molecular Conformation
Nickel / chemistry*
Oxidative Coupling
Stereoisomerism

Substances

Amino Acids
Halogens
Nickel