Deconjugative α‑Alkylation of Cyclohexenecarboxaldehydes: An Access to Diverse Terpenoids
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Chahboun, Rachid; Botubol-Ares, José Manuel; Durán-Peña, María Jesús; Jiménez, Fermín; Alvarez-Manzaneda Roldán, Ramón Jesús; [et al.]Fecha
2021-06-15Resumen
A general and efficient method for the deconjugative α-alkylation of α,β-unsaturated aldehydes promoted by a synergistic effect between tBuOK and NaH, which considerably increases the reaction rate under mild conditions, is reported. The β,γ-unsaturated aldehyde, resulting from the α-alkylation, is transformed in high yield into the corresponding allyl acetate via a lead(IV) acetate-mediated oxidative fragmentation. This strategy could be used for the construction of the carbon skeleton of a wide variety of alkyl or arylterpenoids.