Oxidation-initiated Nazarov cyclization of vinyl alkoxyallenes
William T Spencer1, Mark D Levin, Alison J Frontier
1Department of Chemistry, University of Rochester, Rochester, New York 14627, USA.
Abstract:
A mild method for the diastereoselective formation of C(4), C(5)-disubstituted cyclopentenones has been developed, involving formation of a pentadienyl cation via diastereoselective oxidation of a vinyl alkoxyallene. Conrotatory electrocyclization provides the cyclopentenone product. The broad scope, mild conditions, and uncommon substitution pattern accessible through this transformation make it a useful addition to the existing repertoire of cyclopentenone synthetic methods.
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