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

Author:
Uchida, Natsuko, Kuwabara, Junpei, Taketoshi, Ayako, Kanbara, Takaki
Source:
Journal of organic chemistry 2012 v.77 no.23 pp. 10631-10637
ISSN:
1520-6904
Subject:
alcohols, aldehydes, amino compounds, carbonyl compounds, catalysts, catalytic activity, chemical reactions, moieties, nitroalkanes, organic chemistry, pyridines
Abstract:
The molecular design, characteristics, and catalytic activity of macrocyclic amino compounds, azacalix[3](2,6)pyridine derivatives, were studied. The introduction of an electron-donating group on the pyridine moiety and bridging amino phenyl group enabled the enhancement of the basicity of azacalix[3](2,6)pyridine up to pKBH₊ = 29.5 in CD₃CN. These derivatives were shown to be efficient catalysts for 1,4-addition reactions of nitroalkanes or primary alcohols to α,β-unsaturated carbonyl compounds and 1,2-addition reactions of nitroalkanes to aromatic aldehydes.
Agid:
5499435