Journal of the Chemical Society. Perkin transactions I p. 2458 - 2462 (1980)
Update date:2022-09-26
Topics:
Lee, Cheuk Man
Sammes, Michael P.
Katritzky, Alan R.
The addition of N-(2,6-dimethyl-4-oxopyridin-1-yl)pyridinium salts (2) - (4) to lithium enolates (1) of ketones in tetrahydrofuran at low temperatures gives regiospecifically high yields of 1,4-dihydro-adducts (5) - (7).These are readily isolated and can be decomposed under free-radical conditions, also in high yield, to 4-(α-acylalkyl)pyridines (8) - (10).Unsymmetrical dialkyl ketones give a mixture of two isomeric products, the ratio depending upon reaction conditions and steric factors. αβ-Unsaturated ketones, however, give products resulting from reaction exclusively at the position α' to the carbonyl group.
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Doi:10.1016/0040-4039(80)80077-3
(1980)Doi:10.1080/10426509908044971
(1999)Doi:10.1039/jr9630001345
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(1981)
