Synlett

2-Diethoxyphosphoryl-4-nitroalkanoates-Versatile Intermediates in the Synthesis of α-Alkylidene-γ-lactones and Lactams

E Błaszczyk, H Krawczyk, T Janecki

Index: Blaszczyk, Edyta; Krawczyk, Henryk; Janecki, Tomasz Synlett, 2004 , # 15 p. 2685 - 2688

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Citation Number: 23

Abstract

Abstract Michael addition of various nitroalkanes 7a-f to ethyl (2-diethoxyphosphoryl) acrylate (6) gave 2-diethoxyphosphoryl-4-nitroalkanoates 8a-f. Transformation of the nitro functionality into hydroxy or amino group and cyclization yielded 3-(diethoxyphosphoryl) tetrahydro-2-furanones 11a-e or 3-(diethoxyphosphoryl) pyrrolidin-2-ones 14a-e, respectively. These compounds were then used in Horner-Wadsworth-Emmons ...