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.
Highlights
Introduction αAmino α-Amino ketones are widespread structural moieties, common to both natural and synthetic significant compounds in medicinal chemistry (Figure (Figure 1) 1) [1,2,3,4]. [1,2,3,4]
Tosylamides from aliphatic aldehydes bearing an α-proton fail to to generate the Crossover acylimines, experimentslikely havedue highlighted that this is under kinetic controltoand that the corresponding to the aptitude of reaction these compounds to isomerize enamides
Reaction pathways between enals and isatin-derived ketimines catalysed by N-heterocyclic carbene (NHC). (A)
Summary
The major regarding successful execution of the aza-benzoin condensation reaction is requirement thatissue the whole process should evolve under kinetical control, in which imines are more should evolve under kinetical control, which imines are the requirement thatBreslow the whole process should evolve kinetical control, in which imines more towards. Intermediates than toto a second molecule of aldehyde, but less reactive with reactive towards. Intermediates than aunder second molecule of aldehyde, but less are reactive reactive towards. Intermediates than to a second molecule of aldehyde, but less reactive the NHC catalyst compared to aldehyde. With the NHC withActivated the NHC catalyst compared to often aldehyde. Are in organic chemistry reagents [20,21,22].as equivalents of carbonyl compounds in reactions with a wide often array employed of nucleophilic compounds in reactions with a wide array of nucleophilic reagents [20,21,22]
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