Stereoselective addition of acetone to the C=N bond of [4.3.0] boron heterobicycles

Abstract

The reaction of N-salicylidene-2-aminophenolate (SAP-H2) derivatives with phenyl boronic acid afforded five new boron bicyclic species in moderate yields, as confirmed by an X-ray study of the boron heterocycle derived from 2-amino-4-chlorophenol. The results also showed that the boron complexes derived from Schiff bases undergo an acetolysis reaction to give the corresponding dioxazaborocines containing all substituents on the same side also in good yields. The structure of one of the addition products was established by X-ray analysis showing that, in the solid state, it exists as a dimeric structure formed by hydrogen bonds.Key words: borocines, tridentate ligands, imines, boronic acids.