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Reversal of facial selectivity in a thia-Claisen rearrangement by incorporation of a vinylic bromine substituent

Ellwood, AR; Mortimer, AJP; Goodman, JM; Porter, MJ; (2013) Reversal of facial selectivity in a thia-Claisen rearrangement by incorporation of a vinylic bromine substituent. ORGANIC & BIOMOLECULAR CHEMISTRY , 11 (43) 7530 - 7539. 10.1039/c3ob41580e. Green open access

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Abstract

Thia-Claisen rearrangements have been carried out using N-benzylpyrrolidine-2-thione and chiral allylic bromides derived from D-mannitol. Introduction of a bromine atom onto the double bond of the allylic bromide reverses the sense of diastereoselectivity in the [3,3]-sigmatropic rearrangement. Density functional theory calculations lead us to rationalise the observed selectivity in terms of a Cíeplak effect.

Type: Article
Title: Reversal of facial selectivity in a thia-Claisen rearrangement by incorporation of a vinylic bromine substituent
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/c3ob41580e
Publisher version: http://dx.doi.org/10.1039/c3ob41580e
Additional information: © The Royal Society of Chemistry 2013. This Open Access Article is licensed under a Creative Commons Attribution 3.0 Unported Licence. PubMed ID: 24091642
UCL classification: UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
UCL > Provost and Vice Provost Offices > VP Innovation and Enterprise
UCL > Provost and Vice Provost Offices > VP Innovation and Enterprise > Innovation Planning
URI: http://discovery.ucl.ac.uk/id/eprint/1410347
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