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  • Title: Highly selective synthesis of pyrazole and spiropyrazoline phosphonates via base-assisted reaction of the Bestmann-Ohira reagent with enones.
    Author: Verma D, Mobin S, Namboothiri IN.
    Journal: J Org Chem; 2011 Jun 03; 76(11):4764-70. PubMed ID: 21504233.
    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 arylidenecycloalkanones 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.
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