Development of Novel Lewis Base Organocatalysts for Asymmetric Synthesis

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.