Application of Nickel(II) Complexes to the Efficient Synthesis of α- or β-Amino Acids

Authors

  • Jiang Wang Center for Drug Discovery and Design, Shanghai Institute of Materia Medica, Shanghai, China
  • Lei Zhang Center for Drug Discovery and Design, Shanghai Institute of Materia Medica, Shanghai, China
  • Hualiang Jiang Shanghai Institute of Materia Medica, China
  • Kaixian Chen State Key Laboratory of Drug Research Shanghai Institute of Materia Medica Shanghai Institutes for Biological Sciences Chinese Academy of Sciences 555 Zu Chong Zhi Road, Shanghai 201203 People's Republic of China
  • Hong Liu State Key Laboratory of Drug Research Shanghai Institute of Materia Medica Shanghai Institutes for Biological Sciences Chinese Academy of Sciences 555 Zu Chong Zhi Road, Shanghai 201203 People's Republic of China. hliu@mail.shcnc.ac.cn

DOI:

https://doi.org/10.2533/chimia.2011.919

Keywords:

Amino acids, C-alkylation reaction, Mannich reaction, Michael reaction, Nickel(ii ) complex, Suzuki reaction

Abstract

Nonproteinogenic α- or β-amino acids have attracted tremendous attention, as they are widely utilized for biological, biochemical, pharmaceutical, and asymmetric chemical investigations. Recently, we developed a series of new strategies for preparing achiral and chiral nickel(ii) complexes for the synthesis of amino acids. We applied these new methods utilizing chiral nickel(ii) complexes for the asymmetric Mannich reaction to synthesize enantiopure α,β-diamino acids, the enantioselective tandem conjugate addition–elimination reaction to prepare glutamic acid derivatives, the Suzuki coupling reaction to yield β2-amino acid derivatives, the asymmetric Mannich reaction to synthesize 3-aminoaspartate, the asymmetric Michael addition reaction to give β-substituted-α,γ-diaminobutyric acid derivatives, the asymmetric alkylation reaction to prepare linear ω-trifluoromethyl containing amino acids, and the asymmetric Michael addition reaction to synthesize syn-β-substituted tryptophans.

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Published

2011-12-14

Issue

Section

Scientific Articles

How to Cite

[1]
J. Wang, L. Zhang, H. Jiang, K. Chen, H. Liu, Chimia 2011, 65, 919, DOI: 10.2533/chimia.2011.919.