An Efficient Synthesis of 2,3-Diaminoacid Derivatives Using Phosphine Catalyst

Yohei Oe¹, Hiroaki Kishimoto², Nahoko Sugioka², Daisuke Harada², Yukio Sato², Tetsuo Ohta¹, Isao Furukawa²

¹Department of Biomedical Information, Faculty of Life and Medical Sciences, Doshisha University, Kyoto, Japan.
²Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyoto, Japan.

DOI: 10.4236/ijoc.2014.43021                

Abstract

Ethyl 2,3-diphthalimidoylpropanoate was effectively synthesized from ethyl propynoate with two equivalents of phthalimide catalyzed by triphenylphosphine in good yield. The choice of reaction media was important for selective synthesis of the desired 2,3-diaminocarboxylic acid derivatives. The reaction is considered to occur through a zwitterionic intermediate derived from the reaction of the α,β-unsaturated ester with triphenylphosphine.

Keywords

Addition, Alkynes, Amino Acids, Catalysis, Multi-Component Reaction

Conflicts of Interest

The authors declare no conflicts of interest.

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