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Aluminum Chloride-Mediated Dieckmann Cyclization for the Synthesis of Cyclic 2-Alkyl-1,3-alkanediones: One-Step Synthesis of the Chiloglottones

Ahlam M. Armaly, Sukanta Bar and Corinna S. Schindler*

*Department of Chemistry, Willard Henry Dow Laboratory, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States, Email: corinnasumich.edu

A. M. Armaly, S. Bar, C. S. Schindler, Org. Lett., 2017, 19, 3958-3961.

DOI: 10.1021/acs.orglett.7b01622 (free Supporting Information)


Abstract

An AlCl3·MeNO2-mediated Dieckmann cyclization reaction of general synthetic utility enables direct access to complex 2-alkyl-1,3-dione building blocks from readily available dicarboxylic acid and acid chloride substrates. This method enables direct access to the chiloglottone plant pheromones from commercially available starting materials in a single synthetic transformation.

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proposed mechanism



Key Words

Dieckmann Condensation, Cyclohexanones, Cyclopentanones


ID: J54-Y2017