Cobalt-Catalyzed, Directed C-H Functionalization/Annulation of Phenylglycinol Derivatives with Alkynes

A new method for cobalt-catalyzed C(sp(2))-H functionalization of phenylglycinol derivatives with terminal and internal alkynes directed by picolinamide auxiliary has been developed. This method offers an efficient and highly regioselective route for the synthesis of 1-hydroxymethyltetrahydroisoquinolines. The reaction employs commercially available Co(II) catalyst in the presence of Mn(III) cooxidant and oxygen as a terminal oxidant and proceeds with full preservation of original stereochemistry.