title: Cationic Iridium/S-Me-BIPAM-Catalyzed Direct Asymmetric Intermolecular Hydroarylation of Bicycloalkenes.
abstract: Highly enantioselective cationic iridium-catalyzed hydroarylation of bicycloalkenes, by carbonyl-directed C-H bond cleavage, was accomplished using a newly synthesized sulfur-linked bis(phosphoramidite) ligand (S-Me-BIPAM). The reaction provides alkylated acetophenone or benzamide derivatives in moderate to excellent yields and good to excellent enantioselectivities. Notably, the hydroarylation reaction of 2-norbornene with N,N-dialkylbenzamide proceeds with excellent enantioselectivity (up to 99% ee) and high selectivity for the mono-ortho-alkylation product.
authors.affiliation: Division of Chemical Process Engineering and Frontier Chemistry Center (FCC), Faculty of Engineering, Hokkaido University, Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628 (Japan).
authors.forename: Tomohiko
authors.initials: T
authors.lastname: Shirai
authors.affiliation: Division of Chemical Process Engineering and Frontier Chemistry Center (FCC), Faculty of Engineering, Hokkaido University, Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628 (Japan). yasuyama@eng.hokudai.ac.jp.
authors.forename: Yasunori
authors.initials: Y
authors.lastname: Yamamoto
keywords: alkenes; alkylation; asymmetric synthesis; iridium; synthetic methods