Study of Heck arylation reaction of non-activated olefins with diazonium salts and their application in stereo controlled total synthesis of neuro excitatory amino acids of the acromelate family

Abstract

The research proposal deals with a detail study of the Heck arylation reaction catalyzed by zerovalent palladium envolving arenediazonium tetrafluoroborates of chiral non-activated olefins of the type 3,4-dehydroprolines. Complementing previous recent studies, several other arenediazonium salts will be tested, including ones bearing electron-withdrawing groups of various types, polyhidroxylated arenediazonium salts and arenediazonium salts derived from pyridine in its free or N-oxide form. The influence of the substitution pattern will also be investigated aiming at future applications of the methodology. The 4-aryl-2,3-dehydroprolines, the final Heck adducts, will be employed in the total stereocontrolled synthesis of the acromelic acids. These compounds are highly neuroexcitatory compounds and of great relevance for farmacological and medicinal studies.