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Fluorine Conformational Effects in Organocatalysis: An Emerging Strategy for Molecular Design
Author(s) -
Zimmer Lucie E.,
Sparr Christof,
Gilmour Ryan
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201102027
Subject(s) - organocatalysis , chemistry , fluorine , biochemical engineering , combinatorial chemistry , computer science , catalysis , enantioselective synthesis , biochemistry , organic chemistry , engineering
M olecular 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 CF bond which functions as a chemically inert steering group for conformational control.