Anderson, JC;
Campbell, IB;
Campos, S;
Shannon, J;
Tocher, DA;
(2015)
Stereoselective synthesis of 1,2-diamine containing indolines by a conjugate addition nitro-Mannich reaction.
Organic & Biomolecular Chemistry
, 13
(1)
170 - 177.
10.1039/c4ob01793e.
Preview |
Text
anderson_article_c4ob01793e.pdf Download (290kB) | Preview |
Abstract
A conjugate addition nitro-Mannich reaction followed by nitro reduction and intramolecular N-arylation gives diastereomerically pure substituted 1,2-diamine containing indolines. Placing the N-arylation cyclisation handle on the imine precursor derived from an ortho-bromine substituted aromatic aldehyde gave the corresponding β-nitroamines in 55-72% yields as single diastereoisomers. Nitro reduction was effected with modified quantities of Zn/HCl and a subsequent Pd(0) catalysed Buchwald Hartwig cyclisation gave indoline products in 40-70% yields as single diastereoisomers.
| Type: | Article |
|---|---|
| Title: | Stereoselective synthesis of 1,2-diamine containing indolines by a conjugate addition nitro-Mannich reaction. |
| Location: | England |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1039/c4ob01793e |
| Publisher version: | http://dx.doi.org/10.1039/c4ob01793e |
| Language: | English |
| Additional information: | This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. This license 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 licenses are available at 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/1453953 |
Archive Staff Only
 |
View Item |
