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Synlett 2011(13): 1940-1946  
DOI: 10.1055/s-0030-1260958
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Hydroxynaphthyl-Substituted α-Amino Acid Derivatives via a Modified Mannich Reaction

Renáta Csütörtökia, István Szatmária, Attila Mándib, Tibor Kurtánb, Ferenc Fülöp*a
a Institute of Pharmaceutical Chemistry and Research Group for Stereochemistry, Hungarian Academy of Sciences, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary
Fax: +36(62)545705; e-Mail: fulop@pharm.u-szeged.hu;
b Department of Organic Chemistry, University of Debrecen, POB 20, 4010 Debrecen, Hungary
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Publication History

Received 13 January 2011
Publication Date:
14 July 2011 (online)

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Abstract

An efficient one-pot synthesis of hydroxynaphthyl-substituted glycine derivatives from 2- or 1-naphthol, glyoxylic acid, and benzyl carbamate via a modified Mannich reaction is described. The enantiomers were successfully separated on analytical and semipreparative HPLC columns. Their absolute configurations were determined by CD analysis supported by TDDFT CD calculations.

Key words

multicomponent reaction - amino acids - Mannich bases - enantioseparation - CD analysis