Dr. Matteo Lanzi

Prof. Arjan Kleij

Photocatalyzed enantiodivergent synthesis of homoallylic and carboxylic acids featuring heterodiaryl quaternary carbon stereocenters

Matteo Lanzi obtained his PhD in Chemical Science in 2019 at the University of Parma (Italy) where he worked on the development of new methodologies in organic chemistry using palladium clusters and photocatalysis. He first moved to the University of Münster (Germany) as a postdoctoral researcher in the group of Prof. Ryan Gilmour. Then he joined the group of Prof. Joanna Wencel-Delord at the University of Strasbourg (France) where he worked on hypervalent compounds chemistries. Awarded with the Juan de la Cierva, Beatriu de Pinós, and then IF-MSCA grants, Matteo joined ICIQ in the group of Prof. Arjan W. Kleij to develop new transition metal-catalyzed asymmetric methodologies for the synthesis of functional compounds. Besides chemistry, he enjoys running and photography.

From 01/10/2023 to



The synthesis of heterodiaryl-based quaternary stereocenters is a very challenging task in organic synthesis, especially in the creation of highly functional scaffolds. Tetrahedral, congested carbons centers bearing two different aryl moieties have great importance for
structure−activity relationship (SAR) studies in pharmaceutical discovery programs. Their presence in biological active natural products makes them fundamental for the future development of new bioactive molecules. Up to now, their synthesis requires unsustainable methodologies that involve high cost, unfavourable step-economy and a negative waste profile features and need highly reactive compounds that only permit low functional groups tolerance. Moreover, the enantioselective synthesis of both product enantiomer requires the use of both catalyst enantiomers raising the cost of the process. Therefore, it is fundamental to develop a simple, scalable and environmentally friendly approach for the enantioselective synthesis of compounds comprising heterodiaryl-quaternary stereocenters and functionalized derivatives. The PEACE project aims to develop a novel photocatalyzed, enantiodivergent synthesis process leading to such heterodiarylated all-carbon stereocenters. The designed dual catalytic cycle of the PEACE project merges Pd and photoredox catalysis to promote the enantioselective construction of new sp3-sp2 carbon-carbon bonds resulting into products featuring a quaternary carbon stereocenter. The enantiodivergent strategy is based on a judicious choice of structurally modular reaction partners with switchable aryl groups. The combination of VCCs (vinyl,aryl-substituted cyclic carbonates) and a new aryl radical precursor offers an innovative enantiodivergent reaction pathway leading to challenging quaternary stereocenters creating impetus in the area of organic synthetic chemistry, and revolutionizing similar synthetic designs in
the pharmaceutical industry.