Novel asymmetric C-C bond formation process promoted by Et(sub 2)AlCl and its application to the stereoselective synthesis of unusual beta-branched Baylis-Hillman adducts

A novel asymmetric carbon-carbon bond formation process based on the application of the Davis-type p-toluenesulfinimines to the tandem vicinal difunctionalization technique is described. The synthetic route involves the use of various Lewis acids to activate p-toluenesulfinimine electrophiles. Experimental results show that the beta-branched (alpha-carbalkoxyvinyl)-cuprates react very well with p-toluenesulfinimines at low temperature when diethylaluminum chloride is added to the reaction system.