Aliev, A;
Anderson, JC;
Corpinot, MK;
Gascoigne, ESJ;
(2018)
Radical cyclisation studies of β-nitroamines from the nitro-Mannich reaction.
Tetrahedron
, 74
(38)
pp. 5458-5474.
10.1016/j.tet.2018.06.022.
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Abstract
A range of novel β-nitroacetamides with an alkenyl- or alkynyl tether were synthesized using the deprotonative or conjugate addition nitro-Mannich reaction. They were subjected to radical denitration-cyclisation with a 10 equivalent excess of tributyltin hydride, catalytic AIBN in refluxing benzene to explore the structural and electronic requirements for efficient cyclisation. Cyclisations of the β-nitroacetamides were successful in most cases, undergoing 5-exo-trig cyclisation to give the desired cyclopentyl or indanyl structures. Radical 1,4-translocation of a phenyl group was observed in several cases. Diastereoselectivity was low, with 2 or 3 of 4 possible diastereoisomers observed in most cases. Further purification by crystallisation allowed the isolation of some as single diastereoisomers. It was found that higher yields were obtained by increasing the substitution or reducing the degrees of freedom of the tether between the nitro group and the radical acceptor.
| Type: | Article |
|---|---|
| Title: | Radical cyclisation studies of β-nitroamines from the nitro-Mannich reaction |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1016/j.tet.2018.06.022 |
| Publisher version: | https://doi.org/10.1016/j.tet.2018.06.022 |
| Language: | English |
| Additional information: | This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions. |
| Keywords: | Cyclisation; Free radical; Indanes; Cyclopentanes; Nitro-Mannich |
| 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/10050669 |
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