Enzymatic Dynamic Kinetic Resolution of Oxazinones: A New Approach to Enantiopure β 2 ‐Amino Acids

• Published in: ChemCatChem
• Main Authors: Berkessel, Albrecht, Jurkiewicz, Ilona, Mohan, Resmi
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2011
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/cctc.201000343; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcctc.201000343; http://onlinelibrary.wiley.com/wol1/doi/10.1002/cctc.201000343/fullpdf

Abstract In the presence of Candida antarctica lipase B, the alcoholytic ring opening of 5‐substituted oxazinones proceeds as kinetic resolution (KR) and affords N ‐acyl β 2 ‐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 β 2 ‐amino acid esters in high enantiomeric purity (up to 96 % ee ). N,C‐double deprotection to afford the β 2 ‐amino acid can be effected without loss of enantiopurity.