DS0304 -

Asymmetric Gold(I) versus Gold(III) Catalysis: a Swiss-Army-Knife – GOLDWAR

Submission summary

Over the last years, gold catalysis has gained considerable significance in organic synthesis, since it comprises atom-economic and highly efficient processes for the transformation of relatively simple substrates into valuable, highly complex molecular architectures. Despite these outstanding advances, the enantioselective variants have not flourished as fast and remain a highly challenging task.

In this context, the GOLDWAR project wishes to embrace experimental and applied studies by gathering the forces of three complementary groups:

1) the group “Catalyse, Synthèse de Biomolécules et Développement durable” in Chimie ParisTech (IRCP, UMR 8247, identified as Partner 1, coordinator: Dr. V. Michelet)
2) the group “Hétérocycles et Peptides : Approche Ciblée, Cancer et Antiogenèse” of the Paris Descartes University (UMR 8638, identified as Partner 2, Prof. P. Belmont), and
3) the “Molecular Design of Transition Metal Pre-Catalysts” group of the Laboratoire de Chimie de Coordination in Toulouse (UPR 8241, identified as Partner 3, Dr. V. César).

This project intends to address some technological barriers and contribute to fundamental research in the field of asymmetric cycloisomerization and domino reactions implying gold(I) and gold(III) catalytic systems, on a first approach, and highly modular chiral carbenic ligands. The ligands will be based on chiral N-Heterocyclic Carbenes (NHCs), as they represent a very effective and robust class of supporting ligands. More specifically, we will focus on the development of highly modular NHC architectures specifically designed to bring the chiral information in close proximity to the metallic center, which represents a key feature for an efficient asymmetric induction in gold catalysis. The target substrates of catalysis will be divided in two main classes, namely the 1,n-enynes and the unsaturated carbonyl/imino derivatives, since their gold(I)- and gold(III)-catalyzed conversion will afford a great molecular complexity. By taking advantage of the different reactivities and catalytic profiles of the NHC-Au(I) and NHC-Au(III) complexes, along with their silver common precursor, this project will allow the elaboration of a complete and general panel of efficient and unprecedented enantioselective catalytic systems towards the preparation of bio-relevant building blocks, precursors of natural products and biologically active molecules.

Project coordination

Véronique MICHELET (Institut de Recherche de Chimie Paris)

The author of this summary is the project coordinator, who is responsible for the content of this summary. The ANR declines any responsibility as for its contents.

Partner

ICN-CNRS COTE D'AZUR Institut Chimie de Nice
UPD-COMETE Université Paris Descartes - Laboratoire Chimie Organique Médicinale et Extractive et Toxicologie Expérimentale
LCC-CNRS Laboratoire de Chimie de Coordination du CNRS
IRCP Institut de Recherche de Chimie Paris

Help of the ANR 426,831 euros
Beginning and duration of the scientific project: - 36 Months

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