Catalytic Enantioselective Rauhut–Currier Reaction Mediated by Lithium Selenolates

Abstract

A catalytic enantioselective intramolecular Rauhut–Currier (IRC) reaction has been developed by using a combination of lithium selenolates and a catalytic amount (10 mol %) of an enantiopure BINOL ligand. The study focused particularly on evaluating the influence of BINOL ligands on the reaction’s outcome. The reaction conditions were optimized to achieve good yields and enantioselectivities. Screening of lithium organoselenolates identified phenyl lithium selenolate (PhSeLi) as the most efficient nucleophile. A variety of bis-α,β-unsaturated compounds were successfully cyclized under these conditions, demonstrating the broad applicability of the method. Detailed studies revealed the crucial role of water in the reaction and the importance of hydrogen bonding and Bro̷nsted acid catalysis in achieving asymmetric induction.