An efficient strategy for the synthesis of α,β-unsaturated enaminones by the nucleophilic addition of N-heterocycles such as indole and imidazoles onto electronically bias alkynones under mild reaction conditions is described. Key feature of this reaction is the chemoselective addition of N-heterocycles onto ynones without affecting the 1° amino groups (aromatic and aliphatic) of 5-aminoindole and tryptamine. The stereochemistry of the products was controlled by the tuning of reaction time. The mechanism of the reaction involves the Michael type addition of N-heterocycles on ynones via allene formation.
Volume 132, 2020
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