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Regioselective synthesis of substituted piperidine-2,4-diones and their derivatives via Dieckmann cyclisations

Marson, CM; Yau, KC; (2015) Regioselective synthesis of substituted piperidine-2,4-diones and their derivatives via Dieckmann cyclisations. Tetrahedron , 71 (39) pp. 7459-7469. 10.1016/j.tet.2015.06.052. Green open access

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Abstract

A flexible route to piperidine-2,4-diones variously substituted at the 6-, 5,6- and 2,6-positions, both with and without 1-substitution, is described; no N-protective group is required. A related regioselective Dieckmann cyclisation is also described that uses Davies' α-methylbenzylamine auxiliary and affords 6-substituted piperidine-2,4-diones enantioselectively.

Type: Article
Title: Regioselective synthesis of substituted piperidine-2,4-diones and their derivatives via Dieckmann cyclisations
Open access status: An open access version is available from UCL Discovery
DOI: 10.1016/j.tet.2015.06.052
Publisher version: http://dx.doi.org/10.1016/j.tet.2015.06.052
Language: English
Additional information: © 2015 Elsevier B.V. After an initial embargo period, this manuscript is made available under a Creative Commons Attribution Non-commercial Non-derivative 4.0 International license (CC BY-NC-ND 4.0). This license allows you to share, copy, distribute and transmit the work for personal and non-commercial use providing author and publisher attribution is clearly stated. Further details about CC BY licenses are available at http://creativecommons.org/ licenses/by/4.0. Access may be initially restricted by the publisher.
Keywords: Dieckmann cyclisation, piperidine-2,4-diones, regioselective synthesis, enantioselective synthesis
UCL classification: UCL
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
URI: https://discovery.ucl.ac.uk/id/eprint/1469560
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