Journal of Organic Chemistry p. 7589 - 7596 (1995)
Update date:2022-08-03
Topics:
Katritzky, Alan R.
Zhang, Guifen
Jiang, Jinlong
Lithiation with butyllithium of (N-(α-ethoxyallyl)benzotriazole (2) (readily prepared in quantitative yield on a large scale from benzotriazole and acrolein diethyl acetal (9)) followed by reaction of lithio derivative 14 with halides, α,β-unsaturated esters, α,β-unsaturated ketones, and aldehydes gave exclusively α-alkylation adducts.These adducts are hydrolyzed under extremely mild conditions, enabling convenient syntheses of vinyl ketones 16 and functionalized vinyl ketones 21, 22, 24, and 27.
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Doi:10.1021/jm950740w
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