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Conjugate addition-initiated Nazarov cyclization.

ABSTRACT: A reaction sequence involving the 1,6-conjugate addition of a nucleophile to a dienyl diketone followed by Nazarov cyclization is described. Several nucleophiles are identified as competent initiators for the sequence. A different reaction outcome is observed when catalytic amounts of nucleophile are employed, involving elimination of the nucleophile after the electrocyclization.

SUBMITTER: Brooks JL

PROVIDER: S-EPMC3178270 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Conjugate addition-initiated Nazarov cyclization.

Brooks Joshua L JL Caruana Patrick A PA Frontier Alison J AJ

Journal of the American Chemical Society 20110722 32

A reaction sequence involving the 1,6-conjugate addition of a nucleophile to a dienyl diketone followed by Nazarov cyclization is described. Several nucleophiles are identified as competent initiators for the sequence. A different reaction outcome is observed when catalytic amounts of nucleophile are employed, involving elimination of the nucleophile after the electrocyclization. ...[more]

PMID: 21780785

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