136411-69-3Relevant academic research and scientific papers
Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides
Bartolo, Nicole D.,Demkiw, Krystyna M.,Read, Jacquelyne A.,Valentín, Elizabeth M.,Yang, Yingying,Dillon, Alexandra M.,Hu, Chunhua T.,Ward, Michael D.,Woerpel
, p. 3042 - 3065 (2022/02/25)
The addition of the highly reactive reagent allylmagnesium halide to α-substituted acyclic chiral ketones proceeded with high stereoselectivity. The stereoselectivity cannot be analyzed by conventional stereochemical models because these reactions do not conform to the requirements of those models. Instead, the stereoselectivity arises from the approach of the nucleophile to the most accessible diastereofaces of the lowest-energy conformations of the ketones. High stereoselectivity is expected, and the stereochemical outcome can be predicted, with conformationally biased ketones that have sterically distinguishable diastereofaces wherein only one face is accessible for nucleophilic addition. The conformations of the ketones can be determined by a combination of computational modeling and, in some cases, structure determination by X-ray crystallography.
The formation of cyclic ethers from diallyldibutyltin and halo ketones catalyzed by tetraethylammonium chloride
Yano,Hatta,Baba,Matsuda
, p. 693 - 696 (2007/10/02)
The cyclization reaction of diallyldibutyltin and α- or γ-halo ketones, especially chloro-substituted ketones, effectively proceeds in the presence of a catalytic amount of tetraethylammonium chloride, producing the corresponding 2-allyloxiranes or 2-ally
