Synthesis of γ-oxo α-amino acids from L-aspartic acid

Article abstract of DOI:10.1016/0040-4020(96)00942-8

The synthesis of different γ-oxo α-amino acids from hexafluoroacetone protected L-aspartic acid chloride 1 via Stille cross coupling reaction is described. Stille reaction of 1 with vinyltributyltin followed by Lewis acid catalyzed intramolecular Michael addition provides access to 4-substituted pipecolic acid derivatives. An efficient synthesis of 5-hydroxy-4-oxo-L-norvaline 7 and a new approach to the 4-oxo-L-ornithine skeleton starting from 1 have been elaborated.