Reversal of regioselection in the rearrangement of cinnamate diol cyclic iminocarbonates

Abstract

The rearrangement of cinnamate diol cyclic iminocarbonates can be regioselectively controlled by using, as the nucleophile, Bu4NBr (for β[benzylic]-nitrogen regioselection) or LiI (for the α-nitrogen isomers). This discovery will expand the synthetic utilities of the cyclic iminocarbonate rearrangement and the asymmetric dihydroxylation processes. (C) 2000 Elsevier Science Ltd.