4.6 Article

Designing Fluorinated Cinchona Alkaloids for Enantioselective Catalysis: Controlling Internal Rotation by a Fluorine-Ammonium Ion gauche Effect (fNCCF)

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 18, 期 7, 页码 2006-2013

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201102859

关键词

alkaloids; conformation analysis; fluorine; gauche effect

资金

  1. Alfred Werner Foundation
  2. Swiss National Science Foundation
  3. ETH Zurich

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The C9 position of cinchona alkaloids functions as a molecular hinge, with internal rotations around the C8 C9 (tau(1)) and C9 C4' (tau(2)) bonds giving rise to four low energy conformers (1; anti-closed, anti-open, syn-closed, and syn-open). By substituting the C9 carbinol centre by a configurationally defined fluorine substituent, a fluorine-ammonium ion gauche effect (sigma(C-H) -> sigma(C-F)*; F-delta-...N+) encodes for two out of the four possible conformers (2). This constitutes a partial solution to the long-standing problem of governing internal rotations in cinchonium-based catalysts relying solely on a fluorine conformational effect.

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