BOROXAZOLIDONES AS SIMULTANEOUS PROTECTION OF THE AMINO AND CARBOXYL GROUP IN α-AMINO ACIDS

Article abstract of DOI:10.1016/S0040-4020(01)92162-3

The synthesis of boroxazolidones 1 from a variety of α-amino acids is given.These compounds 1 show a strong intramolecular coordination between B and the amino group.These heterocycles can serve as protected α-amino acids in which the α-amino and the carboxyl function are simultaneously blocked, while the side chain remains free for further reactions.The boroxazolidines were reconverted into α-amino acids under mild acid conditions.Using this methodology aspartic acid was converted into β-benzyl aspartate and glutamic acid into γ-benzyl glutamate.