Synthesis, stereochemistry, and thermolysis of ss-aminoalkylboranes

Article abstract of DOI:10.1246/cl.1996.213

erythro- and threo-ss-Amino boranes Mes₂BCHMeCHPh-NHPh were synthesized by the reaction of Mes₂BCHMeLi with N-benzylideneaniline. The stereochemistry was determined by chemical derivation into the corresponding cyclic carbamates via ss-amino alcohols. Their thermolysis gave a mixture of the corresponding (E)-enamine and its tautomer, (E)-imine, in sharp contrast to that of ss-hydroxy boranes giving the olefins.