Tetrahedron p. 15215 - 15226 (1998)
Update date:2022-08-11
Topics:
Ahrach, Mohammed
Schneider, Raphael
Gerardin, Philippe
Loubinoux, Bernard
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.
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