Fluorine conformational effects in organocatalysis: an emerging strategy for molecular design
Lucie E Zimmer1, Christof Sparr, Ryan Gilmour
1ETH Zürich, Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, Wolfgang-Pauli-Str. 10, CH-8093 Zürich, Switzerland.
Abstract:
Molecular design strategies that profit from the intrinsic stereoelectronic and electrostatic effects of fluorinated organic molecules have mainly been restricted to bio-organic chemistry. Indeed, many fluorine conformational effects remain academic curiosities with no immediate application. However, the renaissance of organocatalysis offers the possibility to exploit many of these well-described phenomena for molecular preorganization. In this minireview, we highlight examples of catalyst refinement by introduction of an aliphatic C-F bond which functions as a chemically inert steering group for conformational control.
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