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)

Research output: Contribution to journalArticle

11 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.
LanguageEnglish
Pages3571-3573
Number of pages2
JournalTetrahedron Letters
Volume50
Issue number26
DOIs
Publication statusPublished - 1 Jul 2009

Fingerprint

Fluorination
Halogenation
Alkenes
Isomerization
Substrates
butylene
2-butene

Keywords

  • efficient
  • fluoride
  • route

Cite this

Laurenson, J. A. B., Meiries, S., Percy, J. M., Roig, R., University of Leicester (Funder), Engineering and Physical Sciences Research Council (EPSRC) (Funder), & WestCHEM (Funder) (2009). Allylic fluorination via an unusual alkene z/e isomerisation. Tetrahedron Letters, 50(26), 3571-3573. https://doi.org/10.1016/j.tetlet.2009.03.068
Laurenson, J.A.B. ; Meiries, S. ; Percy, J.M. ; Roig, R. ; University of Leicester (Funder) ; Engineering and Physical Sciences Research Council (EPSRC) (Funder) ; WestCHEM (Funder). / Allylic fluorination via an unusual alkene z/e isomerisation. In: Tetrahedron Letters. 2009 ; Vol. 50, No. 26. pp. 3571-3573.
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Laurenson, JAB, Meiries, S, Percy, JM, Roig, R, University of Leicester (Funder), Engineering and Physical Sciences Research Council (EPSRC) (Funder) & WestCHEM (Funder) 2009, 'Allylic fluorination via an unusual alkene z/e isomerisation' Tetrahedron Letters, vol. 50, no. 26, pp. 3571-3573. https://doi.org/10.1016/j.tetlet.2009.03.068

Allylic fluorination via an unusual alkene z/e isomerisation. / Laurenson, J.A.B.; Meiries, S.; Percy, J.M.; Roig, R.; University of Leicester (Funder); Engineering and Physical Sciences Research Council (EPSRC) (Funder); WestCHEM (Funder).

In: Tetrahedron Letters, Vol. 50, No. 26, 01.07.2009, p. 3571-3573.

Research output: Contribution to journalArticle

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Laurenson JAB, Meiries S, Percy JM, Roig R, University of Leicester (Funder), Engineering and Physical Sciences Research Council (EPSRC) (Funder) et al. Allylic fluorination via an unusual alkene z/e isomerisation. Tetrahedron Letters. 2009 Jul 1;50(26):3571-3573. https://doi.org/10.1016/j.tetlet.2009.03.068