1262967-63-4Relevant academic research and scientific papers
α,α-Diarylprolinol-derived chiral ionic liquids: Recoverable organocatalysts for the domino reaction between α,β-enals and N-protected hydroxylamines
Maltsev, Oleg V.,Kucherenko, Alexandr S.,Chimishkyan, Alexandr L.,Zlotin, Sergei G.
experimental part, p. 2659 - 2670 (2011/01/05)
Chiral ionic liquids bearing α,α-diarylprolinol units were synthesized and applied for the first time as organocatalysts for the domino reaction between α,β-enals and N-protected hydroxylamines involving aza-Michael and intramolecular acetalization steps. Corresponding 5-hydroxy-3-arylisoxazolidines with either an (S)- or (R)-configuration at C-3 were obtained in excellent yields (up to 94%) and with moderate to high enantioselectivities (64 to >99% ee). The ionic liquid supported catalyst can be easily recycled and reused for at least four times without a significant loss of chemical yield or enantioselectivity.
