Novel cinchona alkaloids derivatives and their application as PTCs

Abstract

Cinchona alkaloids are well known to catalyze a huge ammount of reactions, above all in the field of organocatalysis. Basic diversifications of cinchona alkaloids have involved the hydroxi group at C9 and quinoline nitrogen. in this work we syntesized cinchona alkaloids derivatives with modification of the quinoline moiety and introduction of N-anthracenylmethyl function. As a later stage we tested these novel compounds as possible chiral catalysts under phase-transfer conditions. In particular asymmetric alkylation of glycine Schiff base, epoxidation of trans-chalcone, Michael addition of dibenzylmalonate to trans-chalcone and cyclization of 2'hydroxyxhalcone to flavanone are investigated in order to find the scope and limitations of such novel compounds.