Allylic fluorination via an unusual alkene z/e isomerisation

Laurenson, J.A.B. and Meiries, S. and Percy, J.M. and 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). pp. 3571-3573. ISSN 0040-4039

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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.