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.west
ualberta.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
