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Enzymatic Dynamic Kinetic Resolution of Oxazinones: A New Approach to Enantiopure β 2 ‐Amino Acids
Author(s) -
Berkessel Albrecht,
Jurkiewicz Ilona,
Mohan Resmi
Publication year - 2011
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201000343
Subject(s) - kinetic resolution , enantiopure drug , racemization , candida antarctica , chemistry , triethylamine , enantiomer , amino acid , catalysis , lipase , enzyme , organic chemistry , enzyme catalysis , enantiomeric excess , enantioselective synthesis , stereochemistry , biochemistry
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.