Synthesis of Silicon-Containing a-Amino Acids and Hydantoins
R. J. Smith, S. Bratovanov and S. Bienz, Tetrahedron 1997, 53, 13695.
Three new silicon-containing a-amino acids 6 and their respective hydantoin derivatives 8 have been prepared in racemic form. Alkylation of the a-amino cyanoacetate derivative 1 with iodomethyl-substituted silanes 2 to compounds 3, followed by hydrolysis gave the amino acids 4. The subsequent reactions with KOCN and with HCl gave the N-carboamyl derivatives 5 and finally the hydantoins 6. The hydantoins are planned to be subjected to a biotechnological deracemization process.