The epimerization of chiral alpha-amino acids by 2-hydroxy-2-methyl-1-tetralone template - The synthesis, conditions and mechanism of isomerization

Synthesis and epimerization studies Of iminolactoues prepared via reaction of 2-hydroxy-2-methyl-l-tetralone and methyl alaninate or phenylalaninate are described. The stereochemistry and mechanism of epimerization was studied and explained. The enantiomeric purity of the tetralone template is fully...

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Published inSynthesis (Stuttgart) no. 12; pp. 2013 - 2018
Main Authors Pazicky, Marek, Gaspar, Boris, Solladie-Cavallo, Arlette, Salisova, Marta, Bohac, Andrej, Hutta, Milan, Addova, Gabriela
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 14.06.2006
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
iminolactones
chiral oxazinones
alpha-amino acids
epimerizations
mechanism
1,4-OXAZIN-2-ONE
isomerizations
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Summary:Synthesis and epimerization studies Of iminolactoues prepared via reaction of 2-hydroxy-2-methyl-l-tetralone and methyl alaninate or phenylalaninate are described. The stereochemistry and mechanism of epimerization was studied and explained. The enantiomeric purity of the tetralone template is fully transformed to enantiomeric excess of all diastereomeric products. Deracemization of unnatural alpha-amino acids is considered.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-942401