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
- Alfred Werner Foundation
- Swiss National Science Foundation
- ETH Zurich
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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