Asymmetric Morita-Baylis-Hillman reaction catalyzed by isophoronediamine-derived bis(thio)urea organocatalysts.
New and improved bis(thio)urea catalysts were synthesized from isophoronediamine (IPDA) and tested in the Morita-Baylis-Hillman reaction. The best results were achieved in the reaction of 2-cyclohexen-1-one with cyclohexanecarbaldehyde, using the catalyst depicted above, in combination with a novel base (N,N,N',N'-tetramethylisophoronediamine, TMIPDA) in toluene. The desired Morita-Baylis-Hillman product was obtained in 75% yield and 96% ee.
Berkessel
Albrecht
A
Institute for Organic Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany. berkessel@uni-koeln.de
Roland
Katrin
K
Neudörfl
Jörg M
JM