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Issue 31, 2019
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First aromatic amine organocatalysed activation of α,β-unsaturated ketones

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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

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Publication details

The article was received on 09 May 2019, accepted on 13 Jun 2019 and first published on 16 Jul 2019


Article type: Paper
DOI: 10.1039/C9NJ02392E
New J. Chem., 2019,43, 12233-12240
  • Open access: Creative Commons BY-NC license
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    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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