Oxidation-initiated Nazarov cyclization of vinyl alkoxyallenes |
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| Authors: | Spencer William T Levin Mark D Frontier Alison J |
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| Institution: | Department of Chemistry, University of Rochester, Rochester, New York 14627, USA. |
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| 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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