Synthesis and Function of Artificial Double Helices

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This account mainly describes the synthesis and functions of novel artificial double helices recently developed by our group. We have proposed the first design rationale for artificial double helices with a controlled helicity by employing chiral amidinium-carboxylate salt bridges with <I>m</I>-terphenyl ligands, and synthesized several artificial double helices together with triple- and quadruple-stranded helices. An artificial double helix bearing Pt (II) -acetylide complex moieties has proven effective as a catalyst for the asymmetric cyclopropanation, demonstrating that the chiral space provided by double helices can be effective for asymmetric catalytic reactions. Furthermore, we have serendipitously discovered a spiroborate-based double helicate bearing oligophenol strands and water-soluble double helices of oligoresorcinols. The oligoresorcinol double helices bound cyclic and linear oligosaccharides in water to form rotaxanes and hetero-double helices, respectively, with a remarkable selectivity for the glucosidic linkage patterns and chain lengths.
社団法人有機合成化学協会の論文
2007-11-01