Lecture: «Noncovalent substrate-directing effects in enantioselective Heck Reactions. Recent applications in organic synthesis»
Prof. Carlos Roque D. Correia (Chemistry Institute, State University of Campinas – UNICAMP)
CiQUS Seminar Room - 12:15 h
The enantioselective Heck arylation of olefins has been the subject of intense studies in the last decades due to its outstanding potential to generate new drugs, functional materials, fragrances, and other important compounds.
In this context, the palladium catalyzed coupling of arenediazonium salts to olefins (Heck-Matsuda reaction) represents a robust and reliable method to access complex intermediates for the synthesis of complex functional and bioactive molecules. The Heck-Matsuda arylations have many advantages over the conventional Heck protocols.
Dr. Correia's Group recently reported that non-covalent effects can strongly influence the outcome of these reactions directing the diastereoselectivity and enantioselectivity of these reactions in a pseudo-intramolecular process. The group has also discovered that these effects are not restricted to the Heck-Matsuda, but are also present in other Heck reactions, such as the oxidative Heck reactions.
This lecture will present recent results from his laboratory to perform effective asymmetric Heck-Matsuda reactions employing chiral N,N-ligands, to synthesize challenging chiral tetrasubstituted tertiary centers, and quaternary spiro stereogenic centers, together with applications in the enantioselective total synthesis of pharmacologically active compounds, such as verapamil and VPC01091 –a clinical candidate for the treatment of multiple sclerosis
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