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University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, UK
E-mail: veronique.gouverneur@chem.ox.ac.uk
; Fax: +44 (0)1865 275 644
Org. Biomol. Chem., 2008,6, 1731-1733
DOI:
10.1039/B803888K
Received
06 Mar 2008,
Accepted
20 Mar 2008
First published online
03 Apr 2008
The electrophilic fluorodesilylation of enantioenriched allenylsilanes proceeds with efficient transfer of chirality. The silylation–fluorination of propargylic alcohols occurs with overall retention of stereochemistry, a result consistent with a stereospecific anti SE2′ mechanism for the fluorination step.