Asymmetric Synthesis of Axially Dissymmetric 1,1-Binaphthyls via an Intramolecular Ullmann Coupling Reaction of (R)- and (S)-2,2'-Bis(1-bromo-2-naphthylcarbonyloxy)-1,1'-binaphthyl

Article abstract of DOI:10.1246/bcsj.54.3522

An Ulmann reaction of the chiral bifunctional substrate containing two 1-bromo-2-naphthyl moieties, (S)-2,2'-bis(1-bromo-2-naphthylcarbonyloxy)-1,1'-binaphthyl, gives an intramolecularly coupled 12-membered cyclic diester in a 36 percent isolated yield.The intramolecular coupling reaction prodeeds with virtually complete diastereoselectivity to induce S-chirality into newly formed bond between the two naphthyl units.