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Org Lett. 2008 Sep 18;10(18):4073-6. doi: 10.1021/ol801587u. Epub 2008 Aug 23.

Interrupting the Nazarov cyclization with indoles.

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  • 1Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, USA.

Abstract

A carbon-terminated interrupted Nazarov reaction is described. The trimethylsilyl enol ethers derived from propargyl vinyl ketones undergo selective proton transfer at the distal acetylenic carbon atom to provide allenyl vinyl ketones as transient intermediates. In the presence of indoles, a cascade of reactions is initiated that converts the initially formed pentadienyl cations to cyclopentenones bearing a quaternary alpha carbon atom.

PMID:
18720989
[PubMed - indexed for MEDLINE]
PMCID:
PMC2663042
Free PMC Article
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