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Asymmetric synthesis of piperidines using the nitro-Mannich reaction

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
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 > 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/10118545
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