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A tandem aldol condensation – Diels-Alder cycloaddi tion process is developed to combine isophorone (3,5,5-trimethyl-2-cyclohexen-1-one), ar omatic aldehydes, and methyl acrylate in an efficient stereoselective one-pot synthesis of meth yl (2R,3S)-rel-3-aryl-1,2,3,4,5,6,7,8-octahydro6,6-dimethyl-8-oxo-2-naphthalenecarboxylates using trace quantities of ammonium ions under aqueous conditions. Alternatively, the respective c onjugated dienes which are formed in situ from the condensation of isophorone with the aldehy s can also react with methyl acrylate in a stepwise fashion leading to the same products.

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Et2NH/H2O catalyzed tandem aldol condensation - Diels-Alder cycloaddition sequence for the one-pot synthesis of (2R,3S)-rel-3-aryl-1,2,3,4,5,6,7,8-octahydro-6,6-dimethyl-8-oxo-2-naphthalenecarboxylates