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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

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Oxidation-initiated Nazarov cyclization of vinyl alkoxyallenes.

Spencer William T WT Levin Mark D MD Frontier Alison J AJ

Organic letters 20101214 3

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. ...[more]

PMID: 21155592

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