Chiral, Solvatochromic Schiff Bases Containing the (S)-Proline or (R)-3-Aminopropane-1,2-diol Functionality

Abstract

Chiral 4-nitroaniline derivatives 2a,b containing amino acid and 1,2-diol functionalities have been synthesized by specific nucleophilic substitution of 1-fluoro-4-nitrobenzene (1) with (S)-proline or (R)-3-aminopropane-1,2-diol. Following reduction of the nitro groups under very mild conditions, the corresponding p-phen­ylenediamine derivatives 3a,b were obtained which are very sensitive to oxidation. Thus, 3a,b were converted in situ into chiral, solvatochromic Schiff bases.

Key words

amino acids - amino alcohols - chirality - nucleophilic aromatic substitution - Schiff bases

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17

Schreiter, K.; El Sayed, M.; Walfort, B.; Rüffer, T.; Lang, H.; Spange, S. unpublished results.

21

Spange, S.; Schreiter, K.; Hofmann, K. unpublished results.