Issue 31, 2019

First aromatic amine organocatalysed activation of α,β-unsaturated ketones

Abstract

This work provides an unprecedented example of a chiral aromatic amine used to activate α,β-unsaturated ketones in asymmetric aminocatalysis. Chiral aromatic diamine VII has been efficiently employed, as a proof of concept, in the Michael addition reaction between benzylideneacetones (1a–f) and coumarins (2a–d). The reaction gives rise to warfarin derivatives 3 with promising results using this family of catalysts for the first time. The additional studies performed supported the bifunctional mode of activation of the chiral catalyst VII and the covalent nature of the interactions between the catalyst VII and benzylideneacetones 1.

Graphical abstract: First aromatic amine organocatalysed activation of α,β-unsaturated ketones

Supplementary files

Article information

Article type
Paper
Submitted
09 May 2019
Accepted
13 Jun 2019
First published
16 Jul 2019
This article is Open Access
Creative Commons BY-NC license

New J. Chem., 2019,43, 12233-12240

First aromatic amine organocatalysed activation of α,β-unsaturated ketones

I. G. Sonsona, E. Marqués-López, M. C. Gimeno and R. P. Herrera, New J. Chem., 2019, 43, 12233 DOI: 10.1039/C9NJ02392E

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