Asymmetric Synthesis of the Diasteroisomers of L-1-Indanylglycine and L-1-Benzindanylglycine, χ1,χ2-Constrained Side-Chain Derivatives of L-Phenylalanine and L-2-Naphthylalanine

Article abstract of DOI:10.1016/0957-4166(92)80003-F

The diastereoisomers of L-1-indanylglycine and L-1-benzindanylglycine, novel topographic tools and analogues of phenylalanine and 2-naphthylalanine, were synthesized from a sultam-derived glycine imine synthon alkylated by judicious electrophiles, and subsequent hydrolysis and sultam-cleavage.An X-ray analysis on one alkylation product established the β-configuration.Key Words: side-chain constrained α amino acids; L-1-indanylglycines; L-1-benzindanylglycines.