Novel Rh-Catalyzed Aryl Transfer From Acridinols to α,β-Unsaturated Carbonyl Compounds

Significance

This work represents a novel and useful method for the conjugate arylation of α,β-unsaturated ketones and esters. Hereby, benzyl-protected acridinols, which can be easily obtained by addition of the respective aryl Grignard reagent to 10-benzylacridin-9(10H)-one, were found to be most efficient for aryl group transfer. By using (S,S)-Bn-bod as chiral ligand for the Rh catalyst it is demonstrated that this reaction is also suitable for asymmetric 1,4-additions.