Picture of DNA strand

Pioneering chemical biology & medicinal chemistry through Open Access research...

Strathprints makes available scholarly Open Access content by researchers in the Department of Pure & Applied Chemistry, based within the Faculty of Science.

Research here spans a wide range of topics from analytical chemistry to materials science, and from biological chemistry to theoretical chemistry. The specific work in chemical biology and medicinal chemistry, as an example, encompasses pioneering techniques in synthesis, bioinformatics, nucleic acid chemistry, amino acid chemistry, heterocyclic chemistry, biophysical chemistry and NMR spectroscopy.

Explore the Open Access research of the Department of Pure & Applied Chemistry. Or explore all of Strathclyde's Open Access research...

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

[img]
Preview
PDF (Laurenson-etal-BJOC2013-Multigramme-synthesis)
multigramme_synthesis_and_asymmetric_dihydroxylation.pdf
Final Published Version
License: Creative Commons Attribution 4.0 logo

Download (573kB)| Preview

    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.