Kinetic Resolution of 5-Substituted Oxazinones with Bifunctional Chiral Base/Squaramide Organocatalysts

5-Substituted oxazinones provide N-protected beta(2)-amino acid esters upon alcoholytic ring opening. Thus far, this access to enantiopure beta(2)-amino acids has been restricted to the use of enzymes (hydrolases) as catalysts for the kinetic resolution of racemic 5-substituted oxazinones, and branc...

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Bibliographic Details
Published inSynlett Vol. 28; no. 11; pp. 1278 - 1281
Main Authors Eroeksuez, Serap, Neudoerfl, Joerg M., Berkessel, Albrecht
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 03.07.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
organocatalysis
squaramides
AZLACTONES
kinetic resolution
asymmetric catalysis
oxazinone
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Summary:5-Substituted oxazinones provide N-protected beta(2)-amino acid esters upon alcoholytic ring opening. Thus far, this access to enantiopure beta(2)-amino acids has been restricted to the use of enzymes (hydrolases) as catalysts for the kinetic resolution of racemic 5-substituted oxazinones, and branched alkyl or ortho-substituted aryl groups on the substrate oxazinone's 5-position were typically not tolerated. We herein report that certain bifunctional chiral base/squaramide organocatalysts, in particular those derived from cis-1,2-diaminocyclohexane or 9-amino-9-epi-quinine, allow the first organocatalytic kinetic resolution of this 'difficult' class of oxazinone substrates, affording N-protected beta(2)-amino acid esters with selectivity factors up to 43.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1588852