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

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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

Author affiliations

* 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

Download options Please wait...

Supplementary files

Supplementary information PDF (2185K)

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

Download Citation

RSC Adv., 2018,8, 14829-14832

Permissions

Request permissions

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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

RSC Advances