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A new approach to the nazarov reaction via sequential electrocyclic ring opening and ring closure



A new approach to the nazarov reaction via sequential electrocyclic ring opening and ring closure



Journal of the American Chemical Society 128(29): 9348-9349



Regioselective dichlorocyclopropanation of 2-silyloxydienes furnishes vinylcyclopropanol silyl ethers in good yield. Treatment with silver(I) at room temperature effects disrotatory electrocyclic opening to a 2-chloro-3-silyloxypentadienyl cation, which then undergoes conrotatory (Nazarov) electrocyclization to provide chlorocyclopentenones. This two-step sequence offers a convenient and mild alternative to the standard Nazarov cyclization protocol via a formal 4+1 construction and furnishes products containing useful halogen functionality. In one case possessing a pendant phenyl group, interrupted Nazarov reaction to give a benzohydrindenone was observed.

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Accession: 048084921

Download citation: RISBibTeXText

PMID: 16848467

DOI: 10.1021/ja063421a


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