Electrophilic fluorination of acyclic chiral allylsilanes

ORGN 257

Matthew Tredwell, matthew.tredwell@stcatz.ox.ac.uk and Véronique Gouverneur, veronique.gouverneur@chem.ox.ac.uk. Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, United Kingdom
The synthesis of organofluorine compounds is a rapidly developing area in organic chemistry due to the increasing number of biologically active compounds and their medicinal applications. The electrophilic fluorodesilylation of vinyl-, allenylmethyl- and allylsilanes has been shown to be an efficient methodology for the preparation of a variety of structurally diverse fluorinated compounds. We have initiated a research programme to investigate the diastereoselectivity and chirality transfer for the electrophilic fluorodesilylation of a range of acyclic homochiral allylsilanes. This versatile methodology has allowed for the preparation of a variety of enantiopure fluorinated building blocks. We have further exploited these diastereoselective fluorination reactions and have prepared advanced precursors of fluorinated analogues of Indinavir (a HIV protease inhibitor) and Sphingolipids