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An Overview on the N-Heterocyclic Carbene-Catalyzed Aza-Benzoin Condensation Reaction

1
Department of Chemistry, Università degli Studi di Milano, via Golgi 19, 20133 Milano, Italy
2
Department of Pharmaceutical Sciences, Sezione di Chimica Generale e Organica “A. Marchesini”, Università degli Studi di Milano, via Venezian 21, 20133 Milano, Italy
*
Author to whom correspondence should be addressed.
Catalysts 2018, 8(5), 181; https://doi.org/10.3390/catal8050181
Received: 23 March 2018 / Revised: 19 April 2018 / Accepted: 26 April 2018 / Published: 28 April 2018

Abstract

The N-heterocyclic carbene(NHCs)-catalyzed aza-benzoin condensation reaction is an efficient, single step strategy which employs easily available substrates, such as aldehydes and imines, to provide α-amino ketones. The multifunctionality and high reactivity of α-amino ketones makes these structures attractive for medicinal chemistry and as precursors of a variety of amine derivatives. The different electrophilic characteristics of aldehydes and imines ensure a high regioselective reaction. Enantiomerically-enriched α-amino ketones have been synthesized through stereoselective couplings promoted by chiral N-heterocyclic carbenes. One-pot domino procedures, including an aza-benzoin step, allow valuable complex molecules to be accessed. View Full-Text
Keywords: aza-benzoin condensation; N-heterocyclic carbene (NHC); alpha-aminoketone; organocatalysis; imine; bis(amino)-cyclopropenylidene (BAC) aza-benzoin condensation; N-heterocyclic carbene (NHC); alpha-aminoketone; organocatalysis; imine; bis(amino)-cyclopropenylidene (BAC)
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Albanese, D.C.M.; Gaggero, N. An Overview on the N-Heterocyclic Carbene-Catalyzed Aza-Benzoin Condensation Reaction. Catalysts 2018, 8, 181.

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