Enzymatic Dynamic Kinetic Resolution of Oxazinones: A New Approach to Enantiopure β 2 ‐Amino Acids
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 triethylamin...
| Published in: | ChemCatChem |
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| Main Authors: | , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Wiley
2011
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| Subjects: | |
| 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 |
| Summary: | 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. |
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