Journal of Organic Chemistry p. 3784 - 3790 (1984)
Update date:2022-07-29
Topics:
Banfi, Luca
Bernardi, Anna
Colombo, Lino
Gennari, Cesare
Scolastico, Carlo
The aldol-type condensation of β-(dimethylamino)propionates 3 and 4 with a series of α-alkoxy aldehydes proceeds with unprecedented high stereoselectivity (up to 24:1) to give anti α-methylene-β-hydroxy-γ-alkoxy esters.The best results were obtained when the reaction was carried out in diethyl ether and the ester enolate was allowed to equilibrate to the thermodynamically more stable geometric isomer.
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