Palladium pincer complex catalyzed asymmetric transformations of sulfonimines

ORGN 141

Juhanes Aydin, juhanes@organ.su.se, Olov A. Wallner, Olov.Wallner@bristol.ac.uk, Vilhelm J. Olsson, ville@organ.su.se, and Kalman J. Szabo, kalman@organ.su.se. Department of Organic Chemistry, Stockholm University, Arrhenius Laboratory, Stockholm, SE-10691, Sweden
Allylation of imines is a challenging area in asymmetric catalysis. We have developed new chiral BINOL based pincer complex catalysts for coupling of allyl metal reagents (such as allyl stannanes and boronates) with sulfonimine substrates. It was found that these pincer complexes are highly active catalysts in the studied allylation reactions. We have studied the effects of the g-substituents (R = H, Me, Cl, SMe, SPh etc) on the enantioselection process. Using the appropriate substituent pattern on the BINOL backbones up to 83% ee could be achieved. Preliminary results for coupling of imines with other organic substrates will also be presented.

 

Process R&D, Physical Organic Chemistry, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, March 25, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007