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.

SUBMITTER: Spencer WT 

PROVIDER: S-EPMC3032600 | biostudies-literature | 2011 Feb

REPOSITORIES: biostudies-literature