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Synlett 2001; 2001(3): 0433-0435
DOI: 10.1055/s-2001-11396
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Cyclopentene Anellation on Assorted Heterocyclic Skeletons by Vinylcyclopropane Rearrangement

Alberto Brandi* , Stefano Cicchi, Melanie Brandl, Sergei I. Kozhushkov, Armin de Meijere
  • *Dipartimento di Chimica Organica “U. Schiff”, and Centro di Studio sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni, C.N.R. Università di Firenze, Via G. Capponi 9, 50121 Firenze, Italy; Fax + 39(55)2 47 69 64; E-mail: brandi@chimorg.unifi.it
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Publication Date:
31 December 2001 (online)

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Several α-spirocyclopropanated heterocyclic ketones were converted to the corresponding cyclopentene-anellated heterocycles in moderate to good yields (overall 31-60%) by Wadsworth-Emmons olefination followed by thermal rearrangement of the formed vinylcyclopropanes. In this sequence, the phosphonoacetonitrile was found to be superior to phosphonoacetate in the Wadsworth-Emmons olefinations of tetrahydropyridones.

cyclopropanes - heterocycles - ketones - olefinations - rearrangements - spiro compounds

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