Development of Novel Lewis Base Organocatalysts for Asymmetric Synthesis

该项目旨在设计一种新的手性路易斯碱催化剂家族，用于羰基化合物与烯丙基三氯硅烷试剂的不对称丁基化，以生产具有高水平对映选择性和非对映选择性的支链和线性均烯丙醇。丁基化方法是有机合成领域中一种重要的化学转化方法，然而单步获得目标化合物仍然很困难，需要使用化学计量手性试剂。这种新型催化剂将能够首次将易于制备与优异的反应性结合起来，克服现有体系在范围、选择性和多样性方面的限制。新催化剂的功能将通过对关键中间体进行流线型的对映选择性合成来利用，以构建具有新型作用机制的强抑菌活性的牛角藻烯生物活性类似物。

The aim of the project is to design a new family of chiral Lewis base catalysts for asymmetric crotylation of carbonyl compounds with allyltrichlorosilane reagents to produce branched and linear homoallylic alcohols with high level of enantio- and diastereoselectivity. The crotylation methodology is an important chemical transformation in the field of organic synthesis, however a single-step access to the target compounds remains difficult, requiring the use of stoichiometric chiral reagents. The new catalysts will be able for the first time to combine the ease of preparation with an exceptional reactivity to overcome the limitations of the existing systems in terms of the scope, selectivity and diversity. The power of the new catalysts will be exploited by executing a streamlined enantioselective synthesis of key intermediates towards construction of bioactive analogues of erogorgiaene that showed potent antibacterial activity with a novel mechanism of action.