“…Our candidate for the tethered nitrogen nucleophile for intramolecular 'S N 2' is the anion of an N-benzoylcarbamate, prepared simply by reaction of benzoyl isocyanate with an appropriately positioned hydroxy (Scheme 10). 20,21 Because the reaction with benzoyl isocyanate occurs rapidly under mild and neutral conditions, sensitive substrates such as epoxy alcohols and diol monotriflates can be used, and many of these are available in enantiomerically pure form. As a model, cinnamyl alcohol 62 was converted to its N-benzoylcarbamate derivative, epoxidized, and then treated with sodium hydride to generated the sodium salt of the N-benzoylcarbamate anion, 64.…”