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Chem."],"accepted":{"date-parts":[[2013,11,8]]},"abstract":"<jats:p>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-2<jats:italic>E<\/jats:italic>-enoates reproducibly and at scale (48\u201353%, ca. 300 mmol). Asymmetric dihydroxylation reactions were then used to transform the butenoate, ultimately into all four diastereoisomers of a versatile fluorinated C<jats:sub>4<\/jats:sub> building block at high enantiomeric-enrichment. The (DHQ)<jats:sub>2<\/jats:sub>AQN and (DHQD)<jats:sub>2<\/jats:sub>AQN ligands described by Sharpless were the most effective. 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