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

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• 作者：Mitsuru Kitamura ; Hiroaki Fukuma ; Mitsuaki Kobayashi ; Shinya Okayama ; Tatsuo Okauchi
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：May 6, 2016
• 年：2016
• 卷：81
• 期：9
• 页码：3956-3960
• 全文大小：337K
• 年卷期：0
• ISSN：1520-6904

文摘

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.