화학공학소재연구정보센터
Journal of the American Chemical Society, Vol.132, No.8, 2550-2550, 2010
2-(Acetoxymethyl)buta-2,3-dienoate, a Versatile 1,4-Biselectrophile for Phosphine-Catalyzed (4+n) Annulations with 1,n-Bisnucleophiles (n=1, 2)
A novel PPh3-catalyzed (4 + n) annulation of 2-(acetoxymethyl)buta-2,3-dienoates 1c-c with 1,n-binucleophiles (n = 1, 2) has been developed to provide a facile synthetic method for cyclopentene and 1,2,3,6-tetrahydropyridazine derivatives. The acetate group of 2-(acetoxymethyl)buta-2,3-dienoate is crucial for the Formation of 1,4-biselectrophilic intermediate C, which is recognized to be a 1,4-biselectrophile that can react with 1,n-bisnucleophiles. Deuterium studies also suggest that the reaction pathway involves a proton-transfer process.