4.8 Article

Axial-Chiral Biisoquinoline N,N′-Dioxides Bearing Polar Aromatic C-H Bonds as Catalysts in Sakurai-Hosomi-Denmark Allylation

Journal

ORGANIC LETTERS
Volume 20, Issue 18, Pages 5757-5761

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02457

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Funding

  1. National Science Foundation [CHE1461196]
  2. Florida Institute of Technology

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The design, synthesis, and evaluation of axial-chiral biisoquinolines bearing polar aromatic C-H bonds as Lewis base catalysts are reported. Lewis bases containing the 3,5-bis-(trifluoromethyl)phenyl group were found to be significantly more enantioselective for a wider range of substrates than those bearing aromatic residues that are not strongly electron-deficient in the allylation of aldehydes with allyltrichlorosilane. Also, optically pure 3,3'-dibromo-1,1'-biisoquinoline N,N'-dioxide that has not been previously reported was synthesized as a common catalyst precursor to facilitate the study.

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