Convenient synthetic route to an enantiomerically pure FMOC alpha-amino acid.
A strategy for the facile alpha-amination of carboxylic acid menthyl esters is described. The resulting diastereomers, readily separable, can be individually carried on to each enantiomer of the FMOC alpha-amino acid. A variety of unnatural side chains were compatible with this approach. The menthyl ester was easily removed from the FMOC alpha-amino acid without racemization.
Taber
Douglass F
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
Berry
James F
JF
Martin
Timothy J
TJ
D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002264:Carboxylic Acids; D002625:Chemistry, Organic / Q000379:methods*; D004952:Esters / Q000737:chemistry; D005449:Fluorenes / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008610:Menthol / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism; D013696:Temperature
D000596:Amino Acids; D002264:Carboxylic Acids; D004952:Esters; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D008610:Menthol