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

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2011 Apr 21

PMID 21504233

Citations 3

Authors

Deepti Verma

Shaikh Mobin

Irishi N N Namboothiri

Affiliations

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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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