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An enantioselective tandem reduction/nitro-Mannich reaction of nitroalkenes using a simple thiourea organocatalyst

Anderson, JC; Koovits, PJ; (2013) An enantioselective tandem reduction/nitro-Mannich reaction of nitroalkenes using a simple thiourea organocatalyst. Chemical Science , 4 (7) 2897 - 2901. 10.1039/c3sc50613d. Green open access

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Abstract

There is a continual need for ever more effective and operationally simpler methods for the asymmetric synthesis of nitrogen containing molecules. We report here a generally efficient synthesis of stereochemically defined β-nitroamine building blocks which, through the combination of two catalytic transformations into one tandem process, results in the use of a simpler asymmetric catalyst, less reaction materials, shorter reaction times, circumvents the need for moisture sensitive reaction partners and leads to a wider substrate scope. Using para-methoxy-phenyl (PMP) protected imines, a Hantzsch ester as hydride source and a simple and economic thiourea organocatalyst, we have promoted the nitro-Mannich reaction with a nitroalkene to form anti-β-nitroamines. After protection as their trifluoroacetamides the products can be isolated in good yields (32–83%), high diastereomeric ratios (90 : 10 to >95 : 5) and excellent enantioselectivity (73–99% ee).

Type: Article
Title: An enantioselective tandem reduction/nitro-Mannich reaction of nitroalkenes using a simple thiourea organocatalyst
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/c3sc50613d
Publisher version: http://dx.doi.org/10.1039/c3sc50613d
Language: English
Additional information: Copyright © The Authors 2013. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (http://creativecommons.org/licenses/by/3.0/).
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/1402533
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