Highly Selective Synthesis of Pyrazole and Spiropyrazoline Phosphonates via Base-Assisted Reaction of the Bestmann-Ohira Reagent with Enones

Abstract

Novel carbonylated pyrazole phosphonates have been synthesized as single regioisomers by treating conjugated enones, dienones, tropone, and quinone with the Bestmann-Ohira reagent under KOH/EtOH conditions at room temperature. Through an "interrupted" version of the above reaction, carbonylated spiropyrazoline phosphonates have been synthesized from arylide-necycloalkanones under similar conditions (K(2)CO(3)/EtOH) with absolute regio-and diastereoselectivity. The key structures were confirmed by detailed spectroscopic analysis and X-ray crystallography.