A C3‐symmetric Diphenylethylendiamine‐Based Catalyst in the Asymmetric Michael Addition of α,β‐Unsaturated Ketones with 4‐Hydroxycoumarin and 4‐Hydroxyquinolin‐2‐one
Alessia CIOGLI, Shilashi Badasa Oljira, Martina De Angelis, Simone Manetto, Francesco Fiorentino, Dante Rotili, Luciana Mosca, Daniel Di Risola, Roberto Mattioli, Marco Pierini, Giulia Mazzoccanti
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引用次数: 0
Abstract
Even though the amino‐organo catalysis has been known for decades, the use of chiral C3‐symmetric multi–amino catalysts in asymmetric synthesis is not widespread. Herein, we extended the approach previously employed for the chiral 1,2‐diamino‐cyclohexane to the enantiopure 1,2‐diphenylethylendiammine. The independent activity of each catalytic subunit was also confirmed for this enantiopure motif by offline high‐resolution ESI‐MS experiments. We evaluated the advantages and limitations of this novel approach in the asymmetric Michael addition of α/β‐unsaturated ketones to 4‐hydroxycoumarin and 4‐hydroxyquinolin‐2‐one, achieving up to 95% yield and moderate to good stereocontrol (enantiomeric ratio up to 80:20). In the pool of synthetized molecules, there are two novel compounds, and one was prepared for the first time using organocatalysis. In addition, some of these molecules showed an intrinsic scavenging ability on ABTS•+ radical.
期刊介绍:
The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies.
The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry:
Liebigs Annalen
Bulletin des Sociétés Chimiques Belges
Bulletin de la Société Chimique de France
Gazzetta Chimica Italiana
Recueil des Travaux Chimiques des Pays-Bas
Anales de Química
Chimika Chronika
Revista Portuguesa de Química
ACH—Models in Chemistry
Polish Journal of Chemistry.