Enzymatic Dynamic Kinetic Resolution of Oxazinones: A New Approach to Enantiopure β2‐Amino Acids

Abstract

AbstractIn the presence of Candida antarctica lipase B, the alcoholytic ring opening of 5‐substituted oxazinones proceeds as kinetic resolution (KR) and affords N‐acyl β2‐amino acid esters in up to 96 % ee, the remaining oxazinones were obtained in up to 99 % ee. In the presence of triethylamine as racemization catalyst, the enzyme‐catalyzed alcoholytic oxazinone opening proceeds as dynamic kinetic resolution (DKR), affording quantitative yields of N‐protected β2‐amino acid esters in high enantiomeric purity (up to 96 % ee). N,C‐double deprotection to afford the β2‐amino acid can be effected without loss of enantiopurity.