A chiral bicyclo[2.2.2]octa-2,5-diene ligand substituted with the ferrocenyl group and its use for rhodium-catalyzed asymmetric 1,4-addition reactions

Abstract

A chiral diene, (R,R)-Fc,Ph-bod, which bears the ferrocenyl (Fc) group and the phenyl (Ph) group on the bicyclo[2.2.2]octa-2,5-diene skeleton, has been synthesized, and its rhodium complex was examined as a catalyst for the asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones. Its enantioselectivity was generally higher than that observed with (R,R)-Ph-bod, which is C₂ symmetric with two phenyl groups.