Synthesis of 1,3-Amino Alcohols, 1,3-Diols, Amines, and Carboxylic Acids from Terminal Alkynes

• DOI: 10.1021/acs.joc.5b01220
• Publication Date: 2015-07-23T16:09:28Z
• Authors: Mingshuo Zeng; Seth B. Herzon
• Keywords: Reductive amination; Markovnikov's rule

The half-sandwich ruthenium complexes 1-3 activate terminal alkynes toward anti-Markovnikov hydration and reductive under mild conditions. These reactions are believed to proceed via addition of water metal vinylidene intermediates (4). functionalization propargylic alcohols by pathways is challenging owing decomposition the starting material catalytic intermediates. Here we show that catalyst 2 can be employed convert 1,3-diols in high yield with retention stereochemistry at position. method also amenable amine derivatives, thereby establishing a route enantioenriched 1,3-amino alcohol products. We report development formal amination oxidative access linear amines carboxylic acids, respectively, from alkynes. This chemistry expands scope products prepared practical high-yielding metal-catalyzed methods.