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A regio- and stereoisomeric study of allylic alcohol fluorination with a range of reagents

Author(s): S. Bresciani, A. M. Z. Slawin, D. O'Hagan

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.

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ISBN: 0022-1139
Publication Year: 2009
Periodical: Journal of Fluorine Chemistry
Periodical Number: 6
Volume: 130
Pages: 537-543
Author Address: