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


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.

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Y. Oe, T. Inoue, H. Kishimoto, M. Sasaki, T. Ohta and I. Furukawa, "Three-Component Coupling Catalyzed by Phosphine: Preparation of α-Amino γ-Oxo Acid Derivatives," International Journal of Organic Chemistry, Vol. 2 No. 2, 2012, pp. 111-116. doi: 10.4236/ijoc.2012.22017.

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The authors declare no conflicts of interest.


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