Diastereoselective synthesis of polypropionates: Cationic couplings of 4-acetoxy-1,3-dioxanes with crotyl-metal reagents

Article abstract of DOI:10.1016/S0040-4039(98)01464-6

Lewis acids promote the coupling of 4-acetoxy-1,3-dioxanes 1 with crotyl-metal species to generate propionate motifs such as 2. The reactions show a marked dependence on Lewis acid, the crotyl metal species, and the presence and stereochemical disposition of a C5 methyl group. A 1,3-syn methyl relationship is favored in these additions.