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

Stefano Bresciani; Alexandra M. Z. Slawin; David O'Hagan

doi:10.1016/j.jfluchem.2009.03.003

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

Stefano Bresciani, Alexandra M. Z. Slawin, David O'Hagan

Research output: Contribution to journal › Article › peer-review

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	https://doi.org/10.1016/j.jfluchem.2009.03.003
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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10.1016/j.jfluchem.2009.03.003

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title = "A regio- and stereoisomeric study of allylic alcohol fluorination with a range of reagents",

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.",

keywords = "Fluorination reagents, DAST, Deoxo-Fluor (TM), TFEDMA, FLUOLEAD (TM), Dehydroxyfluorination, MEDICINAL CHEMISTRY, FLUORIDES, ALDEHYDES, AGENT",

author = "Stefano Bresciani and Slawin, {Alexandra M. Z.} and David O'Hagan",

year = "2009",

month = jun,

doi = "10.1016/j.jfluchem.2009.03.003",

language = "English",

volume = "130",

pages = "537--543",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier",

number = "6",

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TY - JOUR

T1 - A regio- and stereoisomeric study of allylic alcohol fluorination with a range of reagents

AU - Bresciani, Stefano

AU - Slawin, Alexandra M. Z.

AU - O'Hagan, David

PY - 2009/6

Y1 - 2009/6

N2 - 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.

AB - 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.

KW - Fluorination reagents

KW - DAST

KW - Deoxo-Fluor (TM)

KW - TFEDMA

KW - FLUOLEAD (TM)

KW - Dehydroxyfluorination

KW - MEDICINAL CHEMISTRY

KW - FLUORIDES

KW - ALDEHYDES

KW - AGENT

U2 - 10.1016/j.jfluchem.2009.03.003

DO - 10.1016/j.jfluchem.2009.03.003

M3 - Article

SN - 0022-1139

VL - 130

SP - 537

EP - 543

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

IS - 6

ER -

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

Abstract

Keywords

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