A novel tandem [2 + 2] cycloaddition-Dieckmann condensation with ynolate anions. Efficient synthesis of substituted cycloalkenones and naphthalenes via formal [n + 1] cycloaddition

M. Shindo, Y. Sato, K. Shishido

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Abstract

A novel tandem [2 + 2] cycloaddition-Dieckmann condensation via ynolate anions is described. Ynolate anions are useful for the formation of reactive β-lactone enolates via a pathway not involving the enolization of the corresponding β-lactones. The [2 + 2] cycloaddition of ynolate anions with δ- or σ-keto esters, followed by Dieckmann condensation, gives bicyclic β-lactones, which are easily decarboxylated to produce synthetically useful 2,3-disubstituted cyclopentenones and cyclohexenones in one pot. This tandem reaction was applied to a novel, one-pot synthesis of highly substituted naphthalenes.

Original languageEnglish
Pages (from-to)7818-7824
Number of pages7
JournalJournal of Organic Chemistry
Volume66
Issue number23
DOIs
Publication statusPublished - Nov 16 2001
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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