One-pot synthesis of chiral alcohols from alkynes by CF3SO3H/ruthenium tandem catalysis

Huan Liu; Sensheng Liu; Haifeng Zhou; Qixing Liu; Chunqin Wang

doi:10.1039/C8RA02224K

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One-pot synthesis of chiral alcohols from alkynes by CF₃SO₃H/ruthenium tandem catalysis†

Huan Liu,^a Sensheng Liu,^a Haifeng Zhou,

*^a Qixing Liu^a and Chunqin Wang^a

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* Corresponding authors

^a Research Center of Green Pharmaceutical Technology and Process, Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, China
E-mail: zhouhf@ctgu.edu.cn

Abstract

A practical one-pot synthesis of chiral alcohols from readily available alkynes via tandem catalysis by the combination of CF₃SO₃H and a fluorinated chiral diamine Ru(II) complex in aqueous CF₃CH₂OH is described. Very interestingly, the combination of fluorinated catalysts and solvent exhibits a positive fluorine effect on the reactivity and enantioselectivity. A range of chiral alcohols with wide functional group tolerance was obtained in high yield and excellent stereoselectivity under simple and mild conditions.

This article is part of the themed collection: Editors’ collection: Catalytic Organic Transformations

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Article information

DOI: https://doi.org/10.1039/C8RA02224K
Article type: Paper
Submitted: 14 mar. 2018
Accepted: 12 apr. 2018
First published: 19 apr. 2018
This article is Open Access

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RSC Adv., 2018,8, 14829-14832

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One-pot synthesis of chiral alcohols from alkynes by CF₃SO₃H/ruthenium tandem catalysis

H. Liu, S. Liu, H. Zhou, Q. Liu and C. Wang, RSC Adv., 2018, 8, 14829 DOI: 10.1039/C8RA02224K

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