UCL Discovery
UCL home » Library Services » Electronic resources » UCL Discovery

Stereoselective synthesis of 1,2-diamine containing indolines by a conjugate addition nitro-Mannich reaction.

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. Green open access

[img]
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
Downloads since deposit
81Downloads
Download activity - last month
Download activity - last 12 months
Downloads by country - last 12 months

Archive Staff Only

View Item View Item