A Novel and Efficient Tandem Aldol Condensation–Diels–Alder Reaction Pathway for the Direct Synthesis of Dehydrodecaline Derivatives

Abstract

An efficient direct synthesis of dehydrodecaline derivatives is reported via a tandem aldol condensation–Diels–Alder cycloaddition process under Lewis acidic conditions. Addition of dienophile moieties to conjugated dienes, formed in situ from the condensation of enone 1 with aldehydes, lead to high-yield stereo­selective synthesis of the final endo products in relatively short time periods. Products precipitate upon concentration of the organic phase and are purified by recrystallization.

Key words

tandem reaction - aldol condensation - Diels–Alder reaction - endo addition - Lewis acid catalysis

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