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Updated: Oct 22, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Development of a Carbonyl Cyclopentannulation Reagent Based on a 1,4-Dithiane-Fused Nazarov Reaction
Ellen Demeyere1, Kristof Van Hecke2, Johan M Winne1
1Organic Synthesis Research Group, Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 291, Gent9000, Belgium.
Abstract:
Cyclopentanes are common substructures in biologically relevant molecules, but methods for their de novo synthesis from simple building blocks are limited. In this work, we report the development of a novel reagent that allows the direct transformation of ketones and aldehydes into an interesting cyclopentenone moiety. The reagent design hinges on a β-keto phosphonate incorporating a 1,4-dithiane-fused vinylketone. This sulfur heterocycle facilitates a one-pot Horner-Wadsworth-Emmons olefination followed by a Nazarov reaction of the resulting divinylketone.
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