Domino reaction involving the Bestmann–Ohira reagent and α,β-unsaturated aldehydes: efficient synthesis of functionalized pyrazoles

Abstract

A mild, efficient and rapid domino reaction involving the Bestmann-Ohira reagent (BOR) and α,β-unsaturated aldehydes has been developed for the synthesis of densely functionalized vinylpyrazoles. This reaction demonstrates the dual reactivity of BOR as a homologation reagent as well as a cycloaddition partner, thus constituting a domino reaction in an operationally simple procedure. The application of this efficient synthesis of pyrazoles has been demonstrated for the synthesis of phosphonyl analogues of pyrrolopyrazole alkaloids.