title: Entry to Chiral 1,1,2,3-Tetrasubstituted Arylcyclopropanes by Pd(II)-Catalyzed Arylation via Directing Group-Mediated C(sp3)-H Activation.
abstract: Here we report the construction of highly functionalized chiral 1,1,2,3-tetrasubstituted arylcyclopropanes of medicinal chemical importance using Pd(II)-catalyzed arylation via directing group-mediated C(sp3)-H activation. The key aspect for the effective arylation was control of the substrate conformation based on the characteristic steric and stereoelectronic features of cyclopropane by manipulating the protecting group at the hydroxyl. The arylation with good functional group tolerance is pivotal as the first entry to chiral 1,1,2,3-tetrasubstituted arylcyclopropanes with wide variety of aryl groups, including heteroaryl groups.
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University , Kita 12, Nishi 6, Kita-ku, Sapporo 060-0812, Japan.|Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University , Shichonocho 1, Misasagi, Yamashina, Kyoto 607-8412, Japan.
authors.forename: Naoyuki
authors.initials: N
authors.lastname: Hoshiya
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University , Kita 12, Nishi 6, Kita-ku, Sapporo 060-0812, Japan.
authors.forename: Moemi
authors.initials: M
authors.lastname: Kondo
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University , Kita 12, Nishi 6, Kita-ku, Sapporo 060-0812, Japan.
authors.forename: Hayato
authors.initials: H
authors.lastname: Fukuda
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University , Kita 12, Nishi 6, Kita-ku, Sapporo 060-0812, Japan.|Graduate School of Pharmaceutical Sciences, Osaka University , Yamada-oka 1-6, Suita, Osaka 565-0862, Japan.
authors.forename: Mitsuhiro
authors.initials: M
authors.lastname: Arisawa
authors.affiliation: Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University , Shichonocho 1, Misasagi, Yamashina, Kyoto 607-8412, Japan.
authors.forename: Jun'ichi
authors.identifier: 0000-0002-7012-3482
authors.initials: J
authors.lastname: Uenishi
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University , Kita 12, Nishi 6, Kita-ku, Sapporo 060-0812, Japan.|Center for Research and Education on Drug Discovery, Hokkaido University , Kita 12, Nishi 6, Kita-ku, Sapporo 060-0812, Japan.
authors.forename: Satoshi
authors.identifier: 0000-0001-7850-8064
authors.initials: S
authors.lastname: Shuto