2′‐Nitro‐2′‐propen‐1′‐yl 2,2‐Dimethylpropanoate (NPP), A Multiple Coupling Reagent

The title compound 1 (NPP) is prepared from formaldehyde, nitromethane, an pivaloyl chloride. It is shown to be a versatile nitroallylating reagent combining with nucleophiles as different as anilines, indoles, enolates, and organolithium compounds. This is documented by ca. 40 examples (2–30). The mechanism of the reaction is discussed. Some examples of addition of two different nucleophiles to the C3‐moiety of NPP are described (35‐46). This demonstrates the usefulness of NPP as a multiple coupling reagent for convergent syntheses, also of products not containing nitro groups ((Scheme 4)).