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

Verma, Deepti ; Mobin, Shaikh ; Namboothiri, Irishi N. N. (2011) Highly Selective Synthesis of Pyrazole and Spiropyrazoline Phosphonates via Base-Assisted Reaction of the Bestmann–Ohira Reagent with Enones Journal of Organic Chemistry, 76 (11). pp. 4764-4770. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/jo200582z

Related URL: http://dx.doi.org/10.1021/jo200582z

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:121572
Deposited On:19 Jul 2021 10:05
Last Modified:19 Jul 2021 10:05

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