71268-58-1Relevant academic research and scientific papers
α-ALKYLATION AND α-ALKYLIDENATION OF CARBONYL COMPOUNDS BY O-SILYLATED ENOLATE PHENYLTHIOALKYLATION
Paterson, Ian
, p. 4207 - 4220 (2007/10/02)
For many reactions next to a carbonyl group, the use of O-silylated enolate chemistry offers improvements in yield and selectivity over the corresponding reactions of Group I metal enolates.In the case of α-alkylation of carbonyl compounds, Lewis acid (TiCl4 or ZnBr2) promoted phenylthioalkylation of O-silylated enolates 3 by α-chlorosulphides 4 (R3=H, Me, Prn, Pri, Bui, and Me3Si), followed by reductive sulphur removal by Raney nickel, 5->6, is found to be a reliable method for this synthetically important C-C bond forming step.An alternative sulphur elimination pathway via the sulphoxide, 5->7, allows the regio- and stereocontrolled α-alkylidenation of carbonyl compounds.The phenylthioalkylation reaction is applicable to ketones, aldehydes, esters, and lactones.
A study of chiral induction in some diene additions catalyzed by chiral alkoxyaluminum dichlorides
Northcott, Colleen J.,Valenta, Zdenek
, p. 1917 - 1923 (2007/10/02)
A reliable procedure for the preparation of the chiral Lewis acid catalysts, (-)-menthoxy- ((-)-1) and (-)-bornyloxyaluminum dichloride ((-)-2), has been established for the study of diene additions.The geometry of conformationally mobile α,β-unsaturated
