Molecular Design of Organic Superbases, Azacalix[3](2,6)pyridines: Catalysts for 1,2- and 1,4-Additions

摘要

The molecular design, characteristics, andncatalytic activity of macrocyclic amino compounds, azacalix[3]-n(2,6)pyridine derivatives, were studied. The introduction of annelectron-donating group on the pyridine moiety and bridgingnamino phenyl group enabled the enhancement of the basicitynof azacalix[3](2,6)pyridine up to pKBH+ = 29.5 in CD3CN.nThese derivatives were shown to be efficient catalysts for 1,4-naddition reactions of nitroalkanes or primary alcohols to α,β-nunsaturated carbonyl compounds and 1,2-addition reactions ofnnitroalkanes to aromatic aldehydes.