Isopropylidene acetals: Tether control groups for asymmetric intramolecular Diels-Alder reactions

Article abstract of DOI:10.1016/S0040-4039(97)01708-5

The beneficial influence of appropriately placed tartrate and carbohydrate derived isopropylidene acetal tether control groups, to facilitate the asymmetric synthesis of substituted decalins by intramolecular Diels-Alder reactions, is described. In all cases the cis fused adducts 10, 12, 14, 16 and 18 were formed from an endo transition state in which the isopropylidene acetal also determined the π-facial selectivity. Ring cleavage of appropriate adducts afforded functionalized cyclohexenes.