On July 8, 2015, Jimenez, Jacqueline; Ramirez, JuanCarlos; Huelgas, Gabriela; Melendrez, Ruth; Cabrera-Vivas, Blanca M.; Sansinenea, Estibaliz; Ortiz, Aurelio published an article.Quality Control of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one The title of the article was ‘Syn-effect’ in the diastereoselective alkylation of 3-[(E)-α,β-unsaturated-γ-substituted]-N-acyloxazolidinones. And the article contained the following:
Synthetic methods for the formation of alkenes usually produce the E-alkene because it is more stable. However, in isomerization reaction (double bond migration) that takes place in α, β-unsaturated carbonyl compounds, when these carbonyl compounds are exposed to strong bases, furnish Z-alkenes highly stereoselective depending on the γ-substituent in the α, β-unsaturated carbonyl. This stereoselectivity can be attributed to the known Syn-effect. The synthetic value of this methodol. is the achievement of chiral alc. bearing an electron rich Z-alkene, as well as substituted, which was accomplished via removal of the oxazolidinone moiety under treatment with NaBH4, THF-H2O. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Quality Control of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one
The Article related to syn effect stereoselective alkylation unsaturated acyloxazolidinone, General Organic Chemistry: Synthetic Methods and other aspects.Quality Control of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one
Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem