86541-64-2Relevant academic research and scientific papers
A new imidazole-containing imidazolidinone catalyst for organocatalyzed asymmetric conjugate addition of nitroalkanes to aldehydes
Hojabri, Leila,Hartikka, Antti,Moghaddam, Firouz Matloubi,Arvidsson, Per I.
, p. 740 - 748 (2007)
Herein we report a new organocatalyst for the asymmetric Michael addition of nitroalkanes to α,β-unsaturated aldehydes. This catalyst incorporates a basic imidazole group in addition to the secondary amine responsible for activation of the α,β-unsaturated carbonyl compounds via iminium ion formation. The new organocatalyst is capable of catalyzing the enantioselective carbon-carbon bond formation with a high degree of enantiocontrol providing products in enantiomeric excesses of up to 92% and yields of up to to 91 %. These results constitute the best results so far reported for organocatalyzed Michael additions of nitroalkanes to α,β-unsaturated aldehydes, and provide proof of principle that organocatalysts incorporating two internal basic moieties may find broad application in organocatalyzed Michael additions.
