Abstract
Mannich reaction of imines and sily enol ethers induced by radical cation salts was investigated and a series of β-amino ketones were synthesized. Reverse diastereoselectivity was obtained in the reactions of imines and silyl enol ethers of pentan-2-one and pentan-3-one, respectively, which was rationalized by quantum mechanical calculations. A single electron-transfer mechanism was proposed in which the imine radical cation acts as an electrophilic species in this transformation.
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