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.
Preview |
Text
Anderson_Accepted Conj add nitro Man 071014.pdf Download (415kB) | Preview |
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 |
Archive Staff Only
 |
View Item |
