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

JAB Laurenson, JA Parkinson, JM Percy…

Index: Laurenson, James A. B.; Parkinson, John A.; Percy, Jonathan M.; Rinaudo, Giuseppe; Roig, Ricard Beilstein Journal of Organic Chemistry, 2013 , vol. 9, p. 2660 - 2668

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Citation Number: 2

Abstract

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 C 4 building block at high enantiomeric- ...