Single and double stereoselective fluorination of (E)-allylsilanes.
Acyclic allylic monofluorides were prepared by electrophilic fluorination of branched (E)-allylsilanes with Selectfluor. These reactions proceeded with efficient transfer of chirality from the silylated to the fluorinated stereocentre. Upon double fluorination, an unsymmetrical ethyl syn-2,5-difluoroalk-3-enoic ester was prepared, the silyl group acting as an anti stereodirecting group for the two C-F bond forming events.
Sawicki
Marcin
M
University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. marcin.sawicki@chem.ox.ac.uk
Kwok
Angela
A
Tredwell
Matthew
M
Gouverneur
Véronique
V