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Synthesis 2006(12): 2013-2018  
DOI: 10.1055/s-2006-942401
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Marek Pažickýa, Boris Gášpára, Arlette Solladié-Cavallob, Marta Sališová*a, Andrej Boháč*a, Milan Huttac, Gabriela Addovád
a Comenius University, Faculty of Natural Sciences, Department of Organic Chemistry, Mlynská dolina, 842 15 Bratislava, Slovakia
Fax: +421(2)60296690; e-Mail: salisova@fns.uniba.sk; e-Mail: andrej.bohac@fns.uniba.sk;
b ECPM and Unversité Louis Pasteur, 25 rue Becquerel, 67087 Strasbourg, France
c Comenius University, Faculty of Natural Sciences, Department of Analytical Chemistry, Mlynská dolina, 84215 Bratislava, Slovakia
d Comenius University, Faculty of Natural Sciences, Chemical Institute, Mlynská dolina, 84215 Bratislava, Slovakia
Further Information

Publication History

Received 13 January 2006
Publication Date:
06 June 2006 (online)

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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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