Synthesis of beta-amino acids based on oxidative cleavage of dihydropyridone derivatives.
[reaction: see text] A new method for the synthesis of beta-amino acids based on 2,3-dihydropyridones as starting materials is presented. Conversions of 2,3-dihydropyridones with NaIO4 and subsequently with base gave the corresponding beta-amino acids in a one-pot procedure. The reactions have been monitored by 1H NMR indicating that the beta-amino acids were formed in quantitative yields mostly. This method appears to be of broad scope, as 2-substituted 2,3-dihydropyridones are easily accessible via N-acyliminium ions generated from 4-methoxypyridine.
Ege
Markus
M
Department Pharmazie, Zentrum für Pharmaforschung, LMU München, Butenandtstr. 5-13, Haus C, 81377 München, Germany.
Wanner
Klaus T
KT
D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011728:Pyridones / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D007202:Indicators and Reagents; D011728:Pyridones