Synthesis of orthogonally protected optically pure β-amino acids: Constrained phenylalanine analogs 3-tert-butoxycarbonylamino-1,2,3,4- tetrahydro-2-naphthoic acid benzyl ester

Article abstract of DOI:10.1016/S0040-4039(99)00205-1

The synthesis of orthogonally protected β-amino acid 3-tert- butoxycarbonylamino-1,2,3,4-tetrahydro-2-naphthoic acid benzyl ester (Boc- βAtc-OBn) is described. The route to these constrained phenylalanine analogs features a SmI₂-mediated aziridine cleavage resulting in a β-amino ester. The stereochemistries have been determined by X-ray crystallographic analyses.