Creation of Asymmetric Catalysts Based on New Concept, and Their Application to Efficient Synthesis of Pharmaceutical Lead Compounds

点击翻译按钮获取中文摘要

We developed a chiral heteropolymetallic complex containing a lanthanide metal, alkali metal, and BINOL. This new catalyst promotes the direct enantioselective aldol reaction from unmodified ketones and aldehydes with high enantioselectivity. We also developed a novel chiral ligand, linked BINOL, and found that the zinc complex can promote very efficient C-C bond formation between a hydroxyl ketone and aldehydes or imines. The maximum catalyst turnover was reached up to 20000 with maintaining an excellent enantioselectivity. Moreover, we developed a new sugar-derived catalyst that can promote enantioselective cyanosilylation of ketones and ketoimines with high efficiency. Using these catalyses, we established efficient synthetic route of camptothecin (anticancer drug), oxybutynin (muscarinic receptor antagonist), and sorbinil (aldose reductase inhibitor). These synthetic route have a potential of being applied to industrial synthesis.