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An N-Heterocyclic Carbene-Catalyzed [8 + 3] Annulation of Tropone and Enals via Homoenolate

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journal contribution
posted on 10.11.2006, 00:00 authored by Vijay Nair, Manojkumar Poonoth, Sreekumar Vellalath, Eringathodi Suresh, Rajasekaran Thirumalai
A novel protocol for the annulation of tropone to enals involving nucleophilic heterocyclic carbene (NHC) catalyzed homoenolate formation has been developed. Interestingly, the reaction led to bicyclic δ-lactones instead of the expected γ-spirolactones, presumably by the uncommon [8 + 3] annulation pathway. The strategy works well with a variety of enals.