Achieving molecular diversity by metal-catalyzed tandem reactions

Modern chemical transformations should be based on simple and innovative synthetic processes implying the containment of production costs, wastewaters, and reduced use of organic solvents. This can be attained, inter alia, by tandem (or cascade) reactions which allow for structural modifications of the organic compounds through the formation of several chemical bonds in a single, one-pot operation. 

In the present project we plan to exploit the catalysis exerted by complexes of two transition metals of the IB group, i.e., copper and gold, for establishing novel and efficient synthetic procedures based on tandem reactions from alkenes and alkynes, which we have selected as ideal platforms for metal-catalyzed tandem reactions.

One of the scientific goals of AMODIVE is to trap in a tandem fashion chiral alkyl-copper and boryl-copper intermediates with electrophiles not yet considered in order to create molecular diversity in a streamlined asymmetric fashion. 

We plan to study the enantioselective gold-catalyzed rearrangement of suitably substituted propargyl vinyl ethers and propargyl esters to enable cascade processes entailing a [3.3]-rearrangement and either a Nazarov cyclization or a hydroarylation step, ultimately leading to nonracemic pentannulated N-heterocycles, carbocycles and aromatic structures. Carrying out the reaction in the presence of a (hetero)dienophile would add further chemical complexity to the final compounds

Master Degree in Chemistry and Pharmaceutical Technology in 1990 at the University of Pisa.

-1991-1994 Ph.D Degree-Thesis Title: Reactions of 1,2-epoxides and their application to organic synthesis (Supervisor: Prof. Paolo Crotti).

1994-1996 Post-doc at the University of Pisa with Prof. Franco Macchia

1997 INDIVIDUAL MARIE-CURIE FELLOWSHIP at the Department of Organic and Molecular Inorganic Chemistry, University of Groningen, THE NETHERLANDS (supervisor Prof. Dr. Ben Feringa, Nobel Laureate Chemistry year 2016).

-1998-2002 ASSISTANT PROFESSOR (Ricercatore Universitario)
-2000 recipient of the Ciamician Medal, a prestigious award of the Organic Division of the Italian Chemical Society mainly for his achievements on new catalytic enantioselective carbon-carbon bond formation.
-2002 ASSOCIATE PROFESSOR of Organic Chemistry at the Department of Bioorganic Chemistry, University of Pisa.
-2017 FULL PROFESSOR of Organic Chemistry at the Department of Pharmacy, University of Pisa.

Member of the Editorial Advisory Board of the following Journals: Current Organic Chemistry (Bentham Science) and Molecules (MDPI). Member of the Scientific Committee of the A. Corbella International Summer School on Organic Synthesis (ISOS).

He has 116 publications in international peer-reviewed journals, including the most prestigious journals in chemistry.
Sum of the times cited=3915  (Scopus)
h-index=35 (Scopus)

Research activity: The main interest is about the development of new stereoselective synthetic methodologies. In particular, his research activity has been devoted to
1) Novel approach to the synthesis of heterocyclic scaffolds of biological/pharmaceutical interest
2) Development of new catalytic synthetic processes
3) Asymmetric catalysis using organometallic reagents and strained heterocyclic rings

Website: https://people.unipi.it/mauro_pineschi

Ernesto G. Occhiato graduated in Chemistry in 1989 at the University of Florence and carried out his Ph.D. studies in Chemical Science from 1991 to 1994 at the Department of Organic Chemistry, University of Florence (Italy), spending one year at the Department of Chemistry, University of Toronto (Canada) with Prof. Bryan Jones. After a CNR fellowship and post-doctoral studies from 1995 to 2000, he became Researcher at the University of Florence and from 2011 is Associate Professor of Organic Chemistry at the Department of Chemistry “U. Schiff”, University of Florence. He has the national scientific habilitation as Full Professor in Organic Chemistry from April 4th, 2017.

His scientific interests are focused on the development of novel synthetic methodologies based on transition metal (Pd, Au) and enzyme catalysis for the synthesis of naturally occurring hetero- and carbocyclic compounds and new molecular entities possessing biological activity (enzyme  inhibitors, receptor ligands, and vaccine adjuvants). More recent interests include (a) the synthesis of hetero- and carbocycles by Au(I)-catalyzed cascade processes involving propargyl alcohol derivatives, (b) the synthesis of novel conformationally constrained unnatural amino acids for peptidomimetics, and (c) the synthesis of strigolactone analogues for the control of plant growth. He is author/co-author of 105 papers published in international peer reviewed journals. His h-index is 30.

Website: https://www.unifi.it/p-doc2-0-0-A-3f2a3d31332e29.html