Anderson, JC;
Bouvier-Israel, E;
Rundell, CD;
Zhang, X;
(2021)
Asymmetric synthesis of piperidines using the nitro-Mannich reaction.
Tetrahedron
, 78
, Article 131821. 10.1016/j.tet.2020.131821.
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Abstract
A method for the synthesis of functionalized piperidines containing 3 contiguous stereocentres in the 2-,3- and 4- positions uses a diastereoselective nitro-Mannich to control stereochemistry. The nitro-Mannich reaction between a β-aryl/heteroaryl substituted nitroalkanes and glyoxylate imine provides β-nitro-amines with good selectivity (70:30 to >95:5) for the syn, anti-diastereoisomers. Reductive cyclisation with BF3.OEt2 and Et3SiH gave, after purification, stereochemically pure piperidines in 19–57% yield for ten examples with different 4-aryl/heteroaryl substituents.
| Type: | Article |
|---|---|
| Title: | Asymmetric synthesis of piperidines using the nitro-Mannich reaction |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1016/j.tet.2020.131821 |
| Publisher version: | https://doi.org/10.1016/j.tet.2020.131821 |
| 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: | Piperidine, Nitro-Mannich reaction, Cyclisation, B-nitroamine, Diastereoselective |
| UCL classification: | UCL 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-pp.ucl.ac.uk/id/eprint/10118545 |
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