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.

An overview on the N-heterocyclic carbene-catalyzed Aza-Benzoin condensation reaction / D.C. Albanese, N. Gaggero. - In: CATALYSTS. - ISSN 2073-4344. - 8:5(2018 May). [10.3390/catal8050181]

An overview on the N-heterocyclic carbene-catalyzed Aza-Benzoin condensation reaction

D.C. Albanese;N. Gaggero
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.
alpha-aminoketone; aza-benzoin condensation; Bis(amino)-cyclopropenylidene (BAC); imine; N-heterocyclic carbene (NHC); organocatalysis; catalysis; physical and theoretical chemistry
Settore CHIM/06 - Chimica Organica
Settore CHIM/04 - Chimica Industriale
mag-2018
2018
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/579599
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