Highly enantioselective rhodium-catalyzed asymmetric 1,4-addition reactions of arylboronic acids to acyclic α,β-unsaturated compounds: The formal synthesis of (-)-indatraline

It's do or diene: Stable chiral bicyclo[2.2.1]diene ligands were synthesized from (-)-5-oxobornyl acetate and utilized in the asymmetric 1,4-addition reaction of arylboronic acids with acyclic α,β- unsaturated compounds. Low catalytic loading of the complex, generated in situ from 1 and [{RhCl(C₂H₄)₂}₂], provides adducts in good to excellent yields and excellent enantioselectivities. This method was used for the formal total synthesis of (-)-indatraline.