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

¹ Department of Biomedical Information, Faculty of Life and Medical Sciences, Doshisha University, Kyoto, Japan
² Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyoto, Japan
³ Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyoto, Japan
⁴ Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyoto, Japan
⁵ Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyoto, Japan
⁶ Department of Biomedical Information, Faculty of Life and Medical Sciences, Doshisha University, Kyoto, Japan
⁷ Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyoto, Japan

International Journal of Organic Chemistry·Volume 04 (2014)·Pages 189–194·Published 25 August 2014·DOI10.4236/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 <i>α</i>,<i>β</i>-unsaturated ester with triphenylphosphine.

KeywordsAdditionAlkynesAmino AcidsCatalysisMulti-Component Reaction

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

Abstract

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