Loading...
Search for:
α-β-unsaturated-aldehydes
0.005 seconds
A new imidazole-containing imidazolidinone catalyst for organocatalyzed asymmetric conjugate addition of nitroalkanes to aldehydes
, Article Advanced Synthesis and Catalysis ; Volume 349, Issue 4-5 , 2007 , Pages 740-748 ; 16154150 (ISSN) ; Hartikka, A ; Matloubi Moghaddam, F ; Arvidsson, P. I ; Sharif University of Technology
Wiley-VCH Verlag
2007
Abstract
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...