Tetrahedron Letters

Dual-reagent organocatalysis with a phosphine and electron-deficient alkene: application to the Henry reaction

X Wang, F Fang, C Zhao, SK Tian

Index: Wang, Xiu; Fang, Fan; Zhao, Chen; Tian, Shi-Kai Tetrahedron Letters, 2008 , vol. 49, # 45 p. 6442 - 6444

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Citation Number: 15

Abstract

Triphenylphosphine in combination with methyl acrylate was found to be able to catalyze the Henry (nitroaldol) reaction of various aldehydes and α-keto esters to give the corresponding β-nitroalkanols in good to excellent yields, and a catalytic cycle involving a zwitterionic phosphine–alkene adduct was proposed for this dual-reagent organocatalysis according to the deuterium-labeling experiments with CD3NO2.