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

…, J Kuwabara, A Taketoshi, T Kanbara

Index: Uchida, Natsuko; Kuwabara, Junpei; Taketoshi, Ayako; Kanbara, Takaki Journal of Organic Chemistry, 2012 , vol. 77, # 23 p. 10631 - 10637

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Citation Number: 11

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 p K BH+= 29.5 in CD3CN. These derivatives were shown to be efficient catalysts for 1, 4-addition reactions of ...