Regio and enantioselective Heck-Matsuda reaction with allylic alcohols using non symmetrical ligands

Abstract

The first examples of the enantioselective Heck-Matsuda reaction were describedrecently by the group of Professor Correia. In spite of the good yields andenantiodiferentiation achieved for the desymmetrization of olefins using C2 symmetricbisoxazolines, the regioselective arylation of non-symmetrical substrates still remains adifficult task. To circumvent this problem we propose in this project the evaluation of thenonsymmetrical P,N ligands such phosphite-oxazolines and phophoramidite-oxazolineswhich have been developed in the group of Professor Pfaltz at the University of Basel. Themain objective of this project is to develop straightforward syntheses of enantioenriched aand beta aryl-aldehydes by the Pd-catalyzed arylation of allylic alcohols with aryldiazoniumsalts and its further application in the concise total syntheses of pharmacologically activecompounds. (AU)