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.
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.
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M. Zeng, L. Li, S. B. Herzon, J. Am. Chem. Soc., 2014, 136, 7058-7067.