Iterative asymmetric synthesis of protected anti-1,3-polyols

Article abstract of DOI:10.1016/S0040-4039(99)00645-0

A new general method for the iterative asymmetric synthesis of anti-1,3-polyol chains has been developed. The α,α'-bisalkylation of 2,2-dimethyl-1,3-dioxan-5-one SAMP-hydrazone 1 with benzyloxymethylchloride as the second electrophile leads to virtually diastereo- and enantiopure substituted 2,2-dimethyl-1,3-dioxan-5-ones with good overall yields. Their deoxygenation and conversion into primary iodides affords the electrophile for the further alkylation of 1. In this way the configurations of all new stereogenic centres are controlled by a single auxiliary.