In Tandem Auto‐Sustainable Enantioselective Heck‐Matsuda Reactions Directly from Anilines
Christian Leonardo Herrera, João Santiago, Julio Cezar Pastre, Carlos Roque D. Correia
Abstract
Abstract An in tandem enantioselective Heck‐Matsuda (HM) reaction of cyclic and acyclic olefins directly from anilines is described. The method relies on a process involving the progressive in situ diazotization of the starting anilines followed by a palladium‐catalyzed Heck‐Matsuda arylation using chiral N , N ‐ligands. This intermolecular enantioselective HM arylation strategy was applied to the desymmetrization of three distinct unactivated olefins as proof of concept. The method demonstrates broad substrate scope furnishing the Heck adducts in good to excellent enantiomeric ratios of up to 99:1, high diastereoselectivities (cyclopenten‐3‐ol with >20:1 dr), and good overall yields of up to 82% over 2 or 3 steps. magnified image