ASYMMETRIC SYNTHESIS OF α-AMINO ACIDS BY ALKYLATION OF N--2,5-BIS(METHOXYMETHOXYMETHYL)PYRROLIDINE AND ENANTIOSELECTIVE SYNTHESIS OF PROTECTED (2S,9S)-2-AMINO-8-OXO-9,10-EPOXYDECANOIC ACID

Article abstract of DOI:10.1016/S0040-4020(01)86040-3

Highly diastereoselective alkylation (>=96percent de) of α-lithiated N--trans-2,5-bis(methoxymethoxymethyl)pyrrolidine and subsequent hydrolysis gave various α-amino acids of high optical purity.An unusual amino acid (2S,9S)-2-amino-8-oxo-9,10-epoxydecanoic acid was also synthesized enantioselectively in its N-protected form by using the alkylation of the above chiral glycine amide and asymmetric epoxidation as means of introducing C2 and C9 asymmetric centers, respectively.Aldol condensation reaction of the same lithiated glycine amide was also examined.