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A New Approach to the Nazarov Reaction via Sequential Electrocyclic Ring Opening and Ring Closure

Tina N. Grant and F. G. West*

*Department of Chemistry, University of Alberta, Edmonton, Alta., Canada T6G 2G2, Email: frederick.westualberta.ca

T. N. Grant, F. G. West, J. Am. Chem. Soc., 2006, 128, 9348-9349.

DOI: 10.1021/ja063421a (free Supporting Information)


Abstract

Regioselective dichlorocyclopropanation of 2-silyloxydienes furnishes vinylcyclopropanol silyl ethers in good yield. Treatment with silver(I) at room temperature effects disrotatory electrocyclic opening to a 2-chloro-3-silyloxypentadienyl cation, which then undergoes a Nazarov reaction to provide chlorocyclopentenones.

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proposed mechanism



Key Words

Cyclopropanols, Nazarov Cyclization


ID: J48-Y2006-2250