Abstract
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 S(N)1 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. (c) 2009 Elsevier B.V. All rights reserved.
| Original language | English |
|---|---|
| Pages (from-to) | 537-543 |
| Number of pages | 7 |
| Journal | Journal of Fluorine Chemistry |
| Volume | 130 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - Jun 2009 |
Keywords
- Fluorination reagents
- DAST
- Deoxo-Fluor (TM)
- TFEDMA
- FLUOLEAD (TM)
- Dehydroxyfluorination
- MEDICINAL CHEMISTRY
- FLUORIDES
- ALDEHYDES
- AGENT
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