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Title: Multigramme synthesis and asymmetric dihydroxylation of a 4-fluorobut-2E-enoate
Authors: Laurenson, J. A. B.
Parkinson, J. A.
Percy, J. M.
Rinaudo, G.
Roig, Ricard
First Published: 26-Nov-2013
Publisher: Beilstein-Institut
Citation: Beilstein Journal of Organic Chemistry, 2013, 9, pp. 2660–2668.
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.
DOI Link: 10.3762/bjoc.9.301
ISSN: 1860-5397
Version: Publisher Version
Status: Peer-reviewed
Type: Journal Article
Rights: Copyright © 2013 Laurenson et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (
Appears in Collections:Published Articles, Dept. of Chemistry

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