A Convenient Conversion of Substituted Cyclohexenones into Aryl Methyl 
Ketones

André P. Gehring; Franz Bracher

doi:10.1055/s-0032-1316560

Synthesis, Table of Contents

Synthesis 2012; 44(15): 2441-2447
DOI: 10.1055/s-0032-1316560

paper

A Convenient Conversion of Substituted Cyclohexenones into Aryl Methyl Ketones

André P. Gehring

Department of Pharmacy, Center for Drug Research, Ludwig-Maximilians University Munich, Butenandtstr. 5-13, 81377 Munich, Germany, Fax: +49(89)218077802 Email: franz.bracher@cup.uni-muenchen.de

,

Franz Bracher*

Department of Pharmacy, Center for Drug Research, Ludwig-Maximilians University Munich, Butenandtstr. 5-13, 81377 Munich, Germany, Fax: +49(89)218077802 Email: franz.bracher@cup.uni-muenchen.de

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Abstract

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Abstract

This work describes a straightforward multistep conversion of substrates containing a cyclohexenone moiety into mono-, bi- and tricyclic aryl methyl ketones in one single working process. Crucial steps are the addition of 1-ethoxyvinyllithium to the carbonyl group, followed by acid-catalyzed enol ether hydrolysis, dehydration, and dehydrogenation.

Key words

ketones - acetyl anion equivalents - vinyl ether - carbazole - aromatization

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References

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