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Abstract:

Combining functionalization at a distant position from a reactive site with the creation of several consecutive stereogenic centers, including the formation of a quaternary carbon stereocenter, in acyclic system represents a pinnacle in organic synthesis. Here we report the regioselective Heck arylation of terminal olefins as a distant trigger for the ring-opening of cyclopropanes. This Pd-catalyzed unfolding of strained cycle, driving force of the chain-walking process, remarkably proved its efficiency and versatility, as the reaction proceeded regardless of the molecular distance between the initiation (double bond) and termination (alcohol) sites. Moreover, employing stereodefined polysubstituted cyclopropane vaults allowed to access sophisticated stereoenriched acyclic scaffolds in good yields. Conceptually, we demonstrated that merging catalytically a chain walking process with a selective C–C bond cleavage represents a powerful approach to construct linear skeleton possessing several stereogenic centers.

Bio:

Ilan Marek is Professor at the Schulich Faculty of Chemistry at the Technion – Israel Institute of Technology. Since 2005, he holds the Sir Michael and Lady Sobell Academic Chair, is a member of the French Academy of Sciences and a member of the Israel Academy of Sciences and Humanities. He was educated in France, received his PhD thesis in 1988 from the University Pierre et Marie Curie, Paris, (France) with Prof. Jean F. Normant. After a one-year period as a postdoctoral fellow in Louvain-la-Neuve (Belgium) with Prof. Leon Ghosez, he obtained a research position at the CNRS (Centre National de la recherche Scientifique) at the University Pierre et Marie Curie in France in 1990. After obtaining his Habilitation in Organic Chemistry, he moved to the Technion-Israel Institute of Technology in 1997. Prof. Marek has received several awards and recognitions for his research and teaching.