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

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Abstract

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

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A Highly Active and Air-Stable Ruthenium Complex for the Ambient Temperature Anti-Markovnikov Reductive Hydration of Terminal Alkynes

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

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Key Words

protected primary amines, picoline borane, carboxylic acids, phenyliodonium diacetate

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ID: J42-Y2015