Catalytic Asymmetric Synthesis of Functional Chiral Molucules

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Asymmetric synthesis of chiral molucules of excellent function in a large scale is one of the most important challenges in recent synthetic chemistry. For this purpose, design of a novel catalytic cycle and chiral catalyst is essential. We have found that catalytic chiral diether and amino ether promte the reaction of organolithiums in nonpolar medium. The activation is caused by deaggregation of organolithiums by these donor catalysts. This concept was extended to quite promising reactions as shown below.1. Catalytic asymmetric synthesis of beta-lactam of high ee by the reaction of lithium ester enolate with imine in the presence of 5 mol% chiral amino ether catalyst.2. Catalytic asymmetric synthesis of anines of more than 90% ee by the reaction of organolithium with imines.3. Catalytic asymmetric conjugate reaction of organolithiums to alpha, beta-unsaturated esters was performed in high ee in the presence of chiral diether catalyst.