The use of phosphite-borane triesters as a tether in the diastereoselective ring-closing metathesis of C2-symmetric, 1,3-anti-diol-containing dienes is reported. Studies probing the stability of these tether systems, as well as their synthetic utility as intermediates en route to the synthesis of bioactive small molecules, will also be presented. In particular, the subtle differences in the reactivity profile of these phosphite-borane tethers with respect to their all-O-containing counterparts will be highlighted while illustrating the potential power of both tether systems—used separately or in conjunction—to form complex polyols in a facile, manipulable manner.

Phosphorus-based tether methods in the synthesis of complex polyols

249th National Meeting (2015)

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