Efficient, enantioselective iminium catalysis with an immobilized, recyclable diarylprolinol silyl ether catalyst.
A highly efficient approach for the synthesis, application, and recycling of immobilized diarylprolinol silyl ethers was developed. The MeOPEG-supported Jørgensen-Hayashi catalyst provides unchanged reactivity and selectivity as compared to the homogeneous catalyst, as demonstrated for the Michael addition of nitromethane to alpha,beta-unsaturated aldehydes via iminium activation. In addition, the immobilization allows for a simple, column-free isolation of pure, sensitive aldehyde products and therefore may be useful for application in more complicated syntheses.
Mager
Ina
I
Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, D-93053 Regensburg, Germany.
Zeitler
Kirsten
K
D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D004987:Ethers; D011759:Pyrrolidines; C010509:prolinol