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Radical cyclisation studies of β-nitroamines from the nitro-Mannich reaction

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. Green open access

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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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