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

作者：Kitamura Mitsuru^*; Fukuma Hiroaki; Kobayashi Mitsuaki; Okayama Shinya; Okauchi Tatsuo

来源：Journal of Organic Chemistry, 2016, 81(9): 3956-3960.

DOI：10.1021/acs.joc.6b00534

Bifunctional C-2-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.

• 出版日期2016-5-6