AI Article Synopsis
- The research details the synthesis of bifunctional C2-symmetric 7,7'-dihydroxymethyl-8,8'-biquinolyl using a two-step process involving copper/palladium catalysis and palladium(II)-catalyzed oxidation.
- The final product exhibits stable axial chirality, and optically active versions of the compound were obtained through chiral column separation or further oxidation of a precursor.
- The chirality of the enantiomers was confirmed using the exciton chirality method, ensuring the understanding of their absolute stereochemistry.
Article 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.
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| http://dx.doi.org/10.1021/acs.joc.6b00534 | DOI Listing |
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