SYNTHESIS OF χ,δ-UNSATURATED α-AMINO ACIDS FROM ALLYLSILANES AND GLYCIDYL CATION EQUIVALENTS

Article abstract of DOI:10.1016/S0040-4020(01)89098-0

The synthesis of a series of χ,δ-unsaturated N-protected α-amino acid methylesters from the coupling of different allylsilanes and glycidyl cation equivalents 6 and 7 is described.Reactions with methoxyglycine derivative 6 are induced with BF3*OEt2; in the case of chloroglycine derivative 7 SnCl4 is used as Lewis acid.Reactions are fully regioselective, but show low stereoselectivity.The conversion of the reaction products into unprotected α-amino acids is described for two cases.