Deconjugative α-Alkylation of Cyclohexenecarboxaldehydes: An Access to Diverse Terpenoids.

ABSTRACT: 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.

SUBMITTER: Chahboun R 

PROVIDER: S-EPMC8901105 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature