Three-Component Coupling Catalyzed by Phosphine: Preparation of α-Amino γ-Oxo Acid Derivatives

Yohei Oe, Takeshi Inoue, Hiroaki Kishimoto, Mitsuhiro Sasaki, Tetsuo Ohta, Isao Furukawa

Department of Biomedical Information, Faculty of Life and Medical Sciences, Doshisha University, Kyotanabe, Kyoto 610-0394, Japan.
Department of Biomedical Information, Faculty of Life and Medical Sciences, Doshisha University, Kyotanabe, Kyoto 610-0394, Japan.
Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyotanabe, Kyoto 610-0394, Japan.
Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyotanabe, Kyoto 610-0394, Japan.

DOI: 10.4236/ijoc.2012.22017                

Abstract

The three-component coupling reaction of ethyl propiolate (1), phthalimide (2), and aldehyde (3) catalyzed by tripheny- lphosphine, was developed. A solution of an equivalent amount of 1 and 2 in benzaldehyde (3a) in the presence of 30 mol% of PPh3 was heated at 100?C for 48 h to give N-(1-ethoxycarbonyl-3-oxo-3-phenylpropyl)phthalimide (4a) in 83% yield. This reaction was thought to proceed via vinylphosphonium salt formed from the reaction of ethyl propiolate (1) with triphenylphosphine in situ.

Keywords

Three-Component Coupling; Phosphine; 2-Amino-4-Oxocarboxylic Acid

Conflicts of Interest

The authors declare no conflicts of interest.

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