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

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• 作者：Natsuko Uchida ; Junpei Kuwabara ; Ayako Taketoshi ; Takaki Kanbara
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：December 7, 2012
• 年：2012
• 卷：77
• 期：23
• 页码：10631-10637
• 全文大小：450K
• 年卷期：v.77,no.23(December 7, 2012)
• ISSN：1520-6904

文摘

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 pK_BH⁺ = 29.5 in CD₃CN. These derivatives were shown to be efficient catalysts for 1,4-addition reactions of nitroalkanes or primary alcohols to 伪,尾-unsaturated carbonyl compounds and 1,2-addition reactions of nitroalkanes to aromatic aldehydes.