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J Am Chem Soc. 2006 Jul 26;128(29):9348-9.

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

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1
Department of Chemistry, University of Alberta, Edmonton, Alta., Canada T6G 2G2.

Abstract

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.

PMID:
16848467
DOI:
10.1021/ja063421a
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