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Multigramme synthesis and asymmetric dihydroxylation of a 4-fluorobut-2E-enoate

Laurenson, J A B and Parkinson, J A and Percy, J M and Rinaudo, G and Roig, R (2013) Multigramme synthesis and asymmetric dihydroxylation of a 4-fluorobut-2E-enoate. Beilstein Journal of Organic Chemistry, 9. 2660–2668. ISSN 1860-5397

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Abstract

Esters of crotonic acid were brominated on a multigramme scale using a free radical procedure. A phase transfer catalysed fluorination transformed these species to the 4-fluorobut-2E-enoates reproducibly and at scale (48–53%, ca. 300 mmol). Asymmetric dihydroxylation reactions were then used to transform the butenoate, ultimately into all four diastereoisomers of a versatile fluorinated C4 building block at high enantiomeric-enrichment. The (DHQ)2AQN and (DHQD)2AQN ligands described by Sharpless were the most effective. The development and optimisation of a new and facile method for the determination of ee is also described; 19F{1H} spectra recorded in d-chloroform/diisopropyl tartrate showed distinct baseline separated signals for different enantiomers.