Scandium-Catalyzed C-H Addition of Pyridines to Heteroatom-Functionalized Internal Alkenes

摘要

To date, catalytic selective C-H bond addition to unactivated internal alkene is still a very challenging reaction. Here, we report a general, direct C-H bond addition reaction of pyridines to heteroatom-functionalized internal alkenes. This reaction allows for the construction of ortho-alkylpyridines with single regioselectivity from a wide scope of unactivated internal alkene starting materials bearing oxygen atom at the remote site. The interaction between the oxygen atom and the scandium catalyst plays a crucial role in the reaction. Using this strategy, desymmetrization of cyclopentene has also been realized with exclusive diastereoselectivity and good enantioselectivity.