Asymmetric Induction during the Aminolysis of 5(4H)-Oxazolones from N-Benzoyl Amino Acids; Almost Specific Formation of One Epimer in the Reaction of the Oxazolone from N-Benzoyl-DL-t-leucine with Methyl L-Prolinate

Article abstract of DOI:10.1246/bcsj.61.4161

Asymmetric induction during the aminolysis of 5(4H)-oxazolones from N-benzoyl amino acids was investigated using a series of amino acid esters as amine nucleophiles.The reaction of the oxazolone from N-benzoyl-DL-t-leucine with methyl L-prolinate was found to produce the diastereomeric D-L isomer, almost specifically, under appropriate conditions.