Allylic fluorination via an unusual alkene z/e isomerisation

J.A.B. Laurenson; S. Meiries; J.M. Percy; R. Roig; University of Leicester (Funder); Engineering and Physical Sciences Research Council (EPSRC) (Funder); WestCHEM (Funder)

doi:10.1016/j.tetlet.2009.03.068

Allylic fluorination via an unusual alkene z/e isomerisation

J.A.B. Laurenson, S. Meiries, J.M. Percy, R. Roig, University of Leicester (Funder), Engineering and Physical Sciences Research Council (EPSRC) (Funder), WestCHEM (Funder)

Pure And Applied Chemistry

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

14 Citations (Scopus)

Abstract

The isomerisation of readily available (Z)-4-(para-methoxybenzyloxy)- 1 -chloro-2-butene was achieved under mild conditions to afford the much less accessible E-diastereoisomer. This was an effective Substrate in Sharpless asymmetric dihydroxylation (AD) reactions, delivering highly enantiomerically enriched fluorinated butene triol building blocks.

Original language	English
Pages (from-to)	3571-3573
Number of pages	2
Journal	Tetrahedron Letters
Volume	50
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2009.03.068
Publication status	Published - 1 Jul 2009

Keywords

efficient
fluoride
route

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10.1016/j.tetlet.2009.03.068

Cite this

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title = "Allylic fluorination via an unusual alkene z/e isomerisation",

abstract = "The isomerisation of readily available (Z)-4-(para-methoxybenzyloxy)- 1 -chloro-2-butene was achieved under mild conditions to afford the much less accessible E-diastereoisomer. This was an effective Substrate in Sharpless asymmetric dihydroxylation (AD) reactions, delivering highly enantiomerically enriched fluorinated butene triol building blocks.",

keywords = "efficient, fluoride, route",

author = "J.A.B. Laurenson and S. Meiries and J.M. Percy and R. Roig and {University of Leicester (Funder)} and {Engineering and Physical Sciences Research Council (EPSRC) (Funder)} and {WestCHEM (Funder)}",

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AU - Laurenson, J.A.B.

AU - Meiries, S.

AU - Percy, J.M.

AU - Roig, R.

AU - University of Leicester (Funder)

AU - Engineering and Physical Sciences Research Council (EPSRC) (Funder)

AU - WestCHEM (Funder)

PY - 2009/7/1

Y1 - 2009/7/1

N2 - The isomerisation of readily available (Z)-4-(para-methoxybenzyloxy)- 1 -chloro-2-butene was achieved under mild conditions to afford the much less accessible E-diastereoisomer. This was an effective Substrate in Sharpless asymmetric dihydroxylation (AD) reactions, delivering highly enantiomerically enriched fluorinated butene triol building blocks.

AB - The isomerisation of readily available (Z)-4-(para-methoxybenzyloxy)- 1 -chloro-2-butene was achieved under mild conditions to afford the much less accessible E-diastereoisomer. This was an effective Substrate in Sharpless asymmetric dihydroxylation (AD) reactions, delivering highly enantiomerically enriched fluorinated butene triol building blocks.

KW - efficient

KW - fluoride

KW - route

UR - http://dx.doi.org/10.1016/j.tetlet.2009.03.068

U2 - 10.1016/j.tetlet.2009.03.068

DO - 10.1016/j.tetlet.2009.03.068

M3 - Article

SN - 0040-4039

VL - 50

SP - 3571

EP - 3573

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

Allylic fluorination via an unusual alkene z/e isomerisation

Abstract

Keywords

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Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

Cite this

Allylic fluorination via an unusual alkene z/e isomerisation

Abstract

Keywords

Access to Document

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Projects

Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

Cite this