title: Oxidation-initiated Nazarov cyclization of vinyl alkoxyallenes.
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.
authors.affiliation: Department of Chemistry, University of Rochester, Rochester, New York 14627, USA.
authors.forename: William T
authors.initials: WT
authors.lastname: Spencer
authors.forename: Mark D
authors.initials: MD
authors.lastname: Levin
authors.forename: Alison J
authors.initials: AJ
authors.lastname: Frontier
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000466:Alkadienes; D003517:Cyclopentanes; D014753:Vinyl Compounds; C025947:propadiene; C013905:cyclopentenone