title: Pd(II)-Catalyzed Alkylation of Tertiary Carbon via Directing-Group-Mediated C(sp(3))-H Activation: Synthesis of Chiral 1,1,2-Trialkyl Substituted Cyclopropanes.
abstract: A Pd(OAc)2-catalyzed alkylation reaction of the tertiary carbon of chiral cyclopropane substrates with alkyl iodides and bromides via C(sp(3))-H activation has been developed. This is an elusive example of a C-H activation-mediated alkylation of tertiary carbon to effectively construct a quaternary carbon center. The alkylation proceeded with various alkyl halides, including those of functional groups, to provide a variety of chiral cis- and trans-1,1,2,-trialkyl substituted cyclopropanes of medicinal chemical importance.
authors.affiliation: Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University , Misasagi, Yamashina, Kyoto 607-8412, Japan.
authors.forename: Naoyuki
authors.initials: N
authors.lastname: Hoshiya
authors.affiliation: Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University , Misasagi, Yamashina, Kyoto 607-8412, Japan.
authors.forename: Kei
authors.initials: K
authors.lastname: Takenaka
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.initials: S
authors.lastname: Shuto
authors.affiliation: Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University , Misasagi, Yamashina, Kyoto 607-8412, Japan.
authors.forename: Jun'ichi
authors.initials: J
authors.lastname: Uenishi
mesh_terms: D000478:Alkylation; D002384:Catalysis; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003521:Cyclopropanes; D010165:Palladium