Palladium-catalyzed alpha-arylation of azlactones to form quaternary amino acid derivatives.
[reaction: see text] The synthesis of alpha-aryl-alpha-alkyl amino acid derivatives from alpha-amino acids by the arylation of azlactone derivatives is reported. Arylation of azlactones derived from alanine, valine, phenalanine, phenyl glycine, and leucine all provided good yields of the arylated product. Mechanistic studies of this reaction revealed that a stable complex containing a ligand formed by reaction of dba with the azlactone accounts for a new inhibiting effect of dba when reactions are initiated with Pd(dba)(2).
Liu
Xiaoxiang
X
Yale University, Department of Chemistry, New Haven, Connecticut 06511, USA.
Hartwig
John F
JF
D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D007783:Lactones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010165:Palladium / Q000737:chemistry; D012997:Solvents
D000596:Amino Acids; D007202:Indicators and Reagents; D007783:Lactones; D012997:Solvents; D010165:Palladium