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1.2.1.4.1.1 Lewis Acid Catalyzed Indirect Mannich Reaction

DOI: 10.1055/sos-SD-210-00078

Bernardi, L.; Ricci, A.Science of Synthesis: Multicomponent Reactions, (20141125.

The synthesis of simple β-amino ketones 1 and 2 can be performed efficiently from aldehydes, anilines, and trimethylsilyl enol ethers using bismuth(III) trifluoromethanesulfonate[‌10‌] (Scheme 4) or iodine[‌11‌] (Scheme 5) Lewis acids as catalysts. High catalytic activity and low toxicity are features that make these Lewis acids attractive catalysts in this three-component reaction. Further advantages are low catalyst loading (1 or 2 mol%), no formation of byproducts, and moisture/air tolerance in the case of the iodine-catalyzed reaction. Aliphatic aldehydes, except cyclohexanecarbaldehyde, do not react under these conditions probably due to enamine formation.

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References


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