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

1984; Wiley; Volume: 67; Issue: 1 Linguagem: Inglês

10.1002/hlca.19840670133

1522-2675

Dieter Seebàch, Paul Konchel,

Chemical Synthesis and Reactions

Abstract 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 C 3 ‐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 )).