Concerning the diastereofacial selectivity of the reaction of (E)-β- nitroenones with ketone enolates

Article abstract of DOI:10.1016/S0040-4020(98)00972-7

Stereoselectivity of the reaction of acyclic ketone enolates with (E)- β-nitroenones was investigated according to the nature of the base used to accomplish deprotonation. The stereoselectivity and the regioselectivity of the reaction of ketone enolates with (E)-β-nitroenones could be enhanced by the use of trichlorotitanium enolates, which allowed the formation of diastereomeric mixture of (E)-3-hydroxy-5-nitroalk-4-enones 3 where the amount of product of (l) configuration is increased compared to results obtained with lithium enolates.