A new method for cobalt-catalyzed C­(sp2)–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.

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α-Ethynyl glycine derivatives have a high potential for functionalization by derivatization of the amino acid or acetylene moiety, and, as a result, are important intermediates in the construction of biologically active compounds, including natural products. The main methods for the synthesis of ethynyl glycines and glycinols can be divided into six different transformations: (a) homologations of serinal derivatives, (b) nucleophilic alkynylations of α-imino esters/alcohols or their precur-

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A novel approach to C-quaternary alkynyl glycinols based on the Ritter reaction of acetonitrile with cobalt complexed alkynyl glycols is presented.