Synthesis of 1,3-Amino Alcohols, 1,3-Diols, Amines, and Carboxylic Acids from Terminal Alkynes
Mingshuo Zeng and Seth B. Herzon*
*Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States, Email: seth.herzonyale.edu
M. Zeng, S. B. Herzon, J. Org. Chem., 2015, 80, 8604-8618.
DOI: 10.1021/acs.joc.5b01220 (free Supporting Information)
Half-sandwich ruthenium complexes activate terminal alkynes toward anti-Markovnikov hydration and reductive hydration under mild conditions. Propargylic alcohols can be converted to 1,3-diols in high yield and with retention of stereochemistry at the propargylic position. The method is also amenable to formal anti-Markovnikov reductive amination and oxidative hydration reactions to access linear amines and carboxylic acids, respectively.
see article for more examples
M. Zeng, L. Li, S. B. Herzon, J. Am. Chem. Soc., 2014, 136, 7058-7067.