Organic Letters
Organic Letters
5 years ago

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 SN2′-Cuprate Alkylation Strategy to Skipped Polyol Stereotetrads: Utility of an Oxidative “Function Switch” with Phosphite–Borane Tethers
Jana L. Markley, Paul R. Hanson
The development of a P-tether-mediated, iterative SN2′-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 C2-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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00852

DOI: 10.1021/acs.orglett.7b00852

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