New concepts for the synthesis and reactivity of sulfur ylides

• Applicant: Professor Dr. Nuno Maulide
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2010 to 2017
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 186516469

Sulfur ylides occupy a very important place as classical textbook reagents in organic chemistry. Recently, we have developed a robust concept for the direct synthesis of sulfonium ylides by a one-step ylide transfer that proceeds in high levels of efficiency. We have also discovered a novel reactivity manifold of sulfonium ylides towards gold catalysts that enables a versatile synthesis of polysubstituted furans and furanones bearing quaternary centers.Herein, we propose an extended array of new methodologies for catalytic transformations of sulfur ylides under mild conditions. An innovative cyclopropanation of electron-neutral olefins, that has the potential to proceed with high levels of asymmetric induction and which shall offeran attractive alternative to current state-of-the-art methods involving explosive and hazardous diazo compounds, will be developed. Improved chemistry for ylide transfer shall render those processes sustainable and cheap. In addition, mechanistic and theoretical studies shall provide key insight on the details of these reactions. Finally, an unprecedented allylic isomerisation of allylic esters, encountered in the course of preliminary studies in this field, willbe studied.

• DFG Programme: Research Grants
• International Connection: Austria