Metals in concert: Development of a new multi-component multi-catalysis domino reaction merging the Gold-mediated Meyer-Schuster Rearrangement with the Rh-catalyzed enantioselective conjugate addition of boronic acids

• Applicant: Dr. Steffen Kreß
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2013 to 2015
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 243775761

Domino processes enable resource- and time-effective processes for the realization of structural complexity in (asymmetric) organic synthesis. An emerging and largely unexplored approach in this area is the parallel use of two or more metals and corresponding ligands in one reaction vessel. The aim of this work is the development of a method merging the atom-economic Au-catalyzed rearrangement of simple and highly modular accessible propargylic alcohols with the Rh-catalyzed enantioselective 1,4-Addition of boronic acid derivatives. By this one-pot strategy, the time efforts and the material costs regarding the synthesis of beta-chiral carbonyl compounds will be reduced drastically by avoiding purification steps of the generated intermediates. By variation of the ligand systems mutually compatible catalysts will be determined whose selectivities are examined with respect to the desired domino process. The potential of this method will be probed by varying the steric and electronic properties of the substituents. The development of such processes enables highly flexible preparation of enantiomerically pure building blocks for natural product and drug synthesis.

• DFG Programme: Research Fellowships
• International Connection: Canada
• Host: Professor Mark Lautens, Ph.D.