title: Axially Chiral Bifunctional 8,8'-Biquinolyl: Synthesis of 7,7'-Dihydroxymethyl-8,8'-biquinolyl via Pd-Catalyzed Double C-H Oxidation of 7,7'-Dimethyl-8,8'-biquinolyl.
abstract: Bifunctional C2-symmetric 7,7'-dihydroxymethyl-8,8'-biquinolyl (2) was synthesized in short steps via (i) Cu/Pd-catalyzed homo coupling of 7-methyl-8-bromoquinoline and (ii) Pd(II)-catalyzed double C-H oxidation. Axial chirality of 2 and its synthetic precursor 7,7'-dimethyl-8,8'-biquinolyl (3) is stable. Optically active 2 was obtained through separation of racemic 2 by chiral column HPLC or Pd(II)-catalyzed double C-H oxidation of optically active 3. The absolute stereochemistry of enantiomers of 2 and 3 was determined using the exciton chirality method.
authors.affiliation: Department of Applied Chemistry, Kyushu Institute of Technology , 1-1 Sensuicho, Tobata, Kitakyushu, 804-8550 Japan.
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Kitamura
authors.affiliation: Department of Applied Chemistry, Kyushu Institute of Technology , 1-1 Sensuicho, Tobata, Kitakyushu, 804-8550 Japan.
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Fukuma
authors.affiliation: Department of Applied Chemistry, Kyushu Institute of Technology , 1-1 Sensuicho, Tobata, Kitakyushu, 804-8550 Japan.
authors.forename: Mitsuaki
authors.initials: M
authors.lastname: Kobayashi
authors.affiliation: Department of Applied Chemistry, Kyushu Institute of Technology , 1-1 Sensuicho, Tobata, Kitakyushu, 804-8550 Japan.
authors.forename: Shinya
authors.initials: S
authors.lastname: Okayama
authors.affiliation: Department of Applied Chemistry, Kyushu Institute of Technology , 1-1 Sensuicho, Tobata, Kitakyushu, 804-8550 Japan.
authors.forename: Tatsuo
authors.initials: T
authors.lastname: Okauchi