457612-41-8Relevant academic research and scientific papers
A new methodology for synthesis of a chiral phosphinocarboxylic acid through michael cyclization-aldol tandem reaction of chiral α,β,χ,ψ-unsaturated bisphosphine oxide and application in palladium-catalyzed asymmetric allylic alkylation
Inoue, Hideki,Nagaoka, Yasuo,Tomioka, Kiyoshi
, p. 5864 - 5867 (2007/10/03)
Upon successive treatment with lithium diisopropylamide and then benzaldehyde, a chiral α,β,ψ,ω- unsaturated bisphosphine oxide underwent Michael cyclization-aldol tandem reaction to afford the corresponding endo- α,β-unsaturated cyclic bisphosphine oxides. Sequential stereoselective reduction and Horner-Wadsworth-Emmons olefination gave the corresponding monophosphine oxide. Oxidative conversion of an olefin moiety into a carboxyl group and subsequent deoxygenation of an oxide gave the corresponding chiral phosphinocarboxylic acid, which was successfully applied as a chiral and functionalized monophosphine ligand in a palladium-catalyzed asymmetric allylic alkylation.
