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

Renáta Csütörtöki; István Szatmári; Attila Mándi; Tibor Kurtán; Ferenc Fülöp

doi:10.1055/s-0030-1260958

LETTER

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

Renáta Csütörtöki^a, István Szatmári^a, Attila Mándi^b, Tibor Kurtán^b, 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

Abstract

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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

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Referenzen

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