The Epimerization of Chiral α-Amino Acids by 2-Hydroxy-2-methyl-1-tetra­lone Template - The Synthesis, Conditions and Mechanism of Isomerization

Abstract

Synthesis and epimerization studies of iminolactones prepared via reaction of 2-hydroxy-2-methyl-1-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 α-amino acids is considered.

Key words

epimerizations - isomerizations - α-amino acids - iminolactones - chiral oxazinones - mechanism

References

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