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The development of a P-tether-mediated, iterative S N 2'-cuprate alkylation protocol for the formation of 1,3-skipped polyol stereotetrads is reported. This two-directional synthetic strategy builds molecular complexity from simple, readily prepared C 2 -symmetric dienediols and unites the chemistry of both temporary phosphite-borane tethers and temporary phosphate tethers-through an oxidative "function switch" of the P-tether itself-to generate intermediates that were previously inaccessible via either method alone.

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<i>P</i>-Tether-Mediated, Iterative S<sub>N</sub>2′-Cuprate Alkylation Strategy to Skipped Polyol Stereotetrads: Utility of an Oxidative “Function Switch” with Phosphite–Borane Tethers

P-Tether-Mediated, Iterative SN2′-Cuprate Alkylation Strategy to Skipped Polyol Stereotetrads: Utility of an Oxidative “Function Switch” with Phosphite–Borane Tethers

P-Tether-Mediated, Iterative S_N2′-Cuprate Alkylation Strategy to Skipped Polyol Stereotetrads: Utility of an Oxidative “Function Switch” with Phosphite–Borane Tethers