Catalytic Stereoselective Borylative Transannular Reactions

Identificador:  imarina:6013697

Handle: https://hdl.handle.net/20.500.11797/imarina6013697

Autors:  Sendra, Jana; Manzano, Ruben; Reyes, Efraim; Vicario, Jose L; Fernandez, Elena

Resum:
Medium-sized carbocycles containing an alpha,beta-unsaturated ketone moiety as Michael acceptor site and a ketone moiety as internal electrophilic site are ideal substrates to conduct Cu(I)-catalyzed conjugated borylation followed by electrophilic intramolecular trapping that results into a pioneer transannular borylative ring closing reaction. The relative configuration of three adjacent stereocenters is controlled, giving access to a single diastereoisomer for a wide range of substrates tested. Moreover, when a chiral ligand is incorporated, the reaction provides enantioenriched polycyclic products with up to 99 % ee.