Issue 1, 2015

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

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.

Graphical abstract: Stereoselective synthesis of 1,2-diamine containing indolines by a conjugate addition nitro-mannich reaction

Supplementary files

Article information

Article type
Paper
Submitted
28 Aug 2014
Accepted
17 Oct 2014
First published
20 Oct 2014
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2015,13, 170-177

Author version available

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

J. C. Anderson, I. B. Campbell, S. Campos, J. Shannon and D. A. Tocher, Org. Biomol. Chem., 2015, 13, 170 DOI: 10.1039/C4OB01793E

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