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)

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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 languageEnglish
Pages (from-to)3571-3573
Number of pages2
JournalTetrahedron Letters
Volume50
Issue number26
DOIs
Publication statusPublished - 1 Jul 2009

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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