149795-08-4Relevant articles and documents
Concerning the diastereofacial selectivity of the reaction of (E)-β- nitroenones with ketone enolates
Ahrach, Mohammed,Schneider, Raphael,Gerardin, Philippe,Loubinoux, Bernard
, p. 15215 - 15226 (2007/10/03)
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.
A new approach to β-nitroenones. The first preparation of acyclic β-nitroenones
Schneider,Gerardin,Loubinoux
, p. 3117 - 3124 (2007/10/02)
We describe here a new and mild method of synthesis of acyclic β-nitroenones. Nitroepoxydes IV, prepared by epoxydation of the allylic nitroolefins III, react with silicagel or aluminium isopropoxide according to the substrate, to give the nitroethylenic alcohols V. Their oxydation by PCC under sonication leads to the β-nitroenones VI.
