کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1315009 | 975999 | 2009 | 7 صفحه PDF | دانلود رایگان |
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.
The outcome of the regio- and stereoselectivity of fluorination of diastereoisomers of allylic alcohol 1 with a range of dehydroxyfluorination reagents is reported.Figure optionsDownload as PowerPoint slide
Journal: Journal of Fluorine Chemistry - Volume 130, Issue 6, June 2009, Pages 537–543