Expedient synthesis of threo-beta-hydroxy-alpha-amino acid derivatives: phenylalanine, tyrosine, histidine, and tryptophan.
An expedient synthesis of enantiomerically pure threo-beta-hydroxy-alpha-amino acid derivatives of phenylalanine, tyrosine, histidine, and tryptophan is described. The NBS-mediated radical bromination of the N,N-di-tert-butoxycarbonyl protected alpha-amino acids and subsequent treatment with silver nitrate in acetone provided the trans-oxazolidinones predominantly. Cesium carbonate catalyzed hydrolysis then generated the beta-hydroxy amino acid derivatives in excellent overall yield.
Crich
David
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061, USA. dcrich@uic.edu
Banerjee
Abhisek
A
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002586:Cesium / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D006639:Histidine / Q000737:chemistry; D010649:Phenylalanine / Q000737:chemistry; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry; D014443:Tyrosine / Q000737:chemistry
D000596:Amino Acids; D002586:Cesium; D014443:Tyrosine; D010649:Phenylalanine; D006639:Histidine; D014364:Tryptophan