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Conjugate addition nitro-Mannich reaction of carbon and heteroatom nucleophiles to nitroalkenes

Anderson, JC; Kalogirou, AS; Tizzard, GJ; (2014) Conjugate addition nitro-Mannich reaction of carbon and heteroatom nucleophiles to nitroalkenes. Tetrahedron , 70 (49) 9337 - 9351. 10.1016/j.tet.2014.10.042. Green open access

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Abstract

The conjugate addition nitro-Mannich reactions of ethyl-β-nitroacrylate (1) and β-nitrostyrene (2) with electron rich aromatic nucleophiles, stabilized carbanions, alcohols, amines, thiols, and diphenyl phosphine oxide were investigated. The one pot conjugate addition nitro-Mannich reaction was unsuccessful except for the addition of alkoxides to 2 in alcohol as solvent. Isolation of the conjugate addition products followed by deprotonation with nBuLi and treatment with a simple imine in the presence of TFA led to β-nitroamine derived products. Products derived from 1 spontaneously cyclised in only a few examples and on the whole led to inherently unstable products. Products derived from 2 were isolated as their trifluoroacetamides, gave good yields of single diastereoisomers for aromatic and alkoxide nucleophiles and the structures were verified by single crystal X-ray crystallography. Products derived from amine nucleophiles were isolated in low yields while sulfur nucleophiles gave poor diastereoselectivities.

Type: Article
Title: Conjugate addition nitro-Mannich reaction of carbon and heteroatom nucleophiles to nitroalkenes
Open access status: An open access version is available from UCL Discovery
DOI: 10.1016/j.tet.2014.10.042
Publisher version: http://dx.doi.org/10.1016/j.tet.2014.10.042
Language: English
Additional information: © 2014. This manuscript version is published under a Creative Commons Attribution Non-commercial Non-derivative 4.0 International licence (CC BY-NC-ND 4.0). This licence allows you to share, copy, distribute and transmit the work for personal and non-commercial use providing author and publisher attribution is clearly stated. Further details about CC BY licences are available at http://creativecommons.org/licenses/by/4.0.
Keywords: Nitro-Mannich reaction, Nitroalkenes, Conjugate addition, Diastereoselective, Contiguous stereocentres
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.ucl.ac.uk/id/eprint/1459988
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