| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1315009 | Journal of Fluorine Chemistry | 2009 | 7 Pages |
A range of dehydroxyfluorination reagents was reacted with separate diastereoisomers of a chiral allylic alcohol to explore both the regio- and stereoselectivity ratios of direct versus allylic fluorination. The allylic alcohol stereoisomers gave the same predominant fluorinated diastereoisomer indicating that the reaction proceeds with a significant SN1 component via an allylic carbocation intermediate, which is quenched by fluoride ion, predominantly from the least hindered face. None of the reagents displayed very high regio- or stereoselectivity, although in all cases the allylic fluorination products predominated.
Graphical abstractThe outcome of the regio- and stereoselectivity of fluorination of diastereoisomers of allylic alcohol 1 with a range of dehydroxyfluorination reagents is reported.Figure optionsDownload full-size imageDownload as PowerPoint slide
