Next Article in Journal
Production of Added-Value Chemical Compounds through Bioconversions of Olive-Mill Wastewaters Blended with Crude Glycerol by a Yarrowia lipolytica Strain
Next Article in Special Issue
General, Practical and Selective Oxidation Protocol for CF3S into CF3S(O) Group
Previous Article in Journal
9-Norlignans: Occurrence, Properties and Their Semisynthetic Preparation from Hydroxymatairesinol
Previous Article in Special Issue
Copper-Promoted Cross-Coupling Reactions for the Synthesis of Aryl(difluoromethyl)phosphonates Using Trimethylsilyl(difluoromethyl)phosphonate
Article Menu
Issue 2 (January-2) cover image

Export Article

Open AccessArticle
Molecules 2019, 24(2), 221;

Asymmetric Electrophilic Difluoromethylthiolation of Indanone-Based β-Keto Esters Using Difluoromethanesulfonyl Hypervalent Iodonium Ylides

Department of Nanopharmaceutical Sciences, Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan
CNRS, UMR 6014 COBRA, Normandie Université, 1 Rue Tesnière, F-76821 Mont-Saint-Aignan Cedex, France
Institute of Advanced Fluorine-Containing Materials, Zhejiang Normal University, 688 Yingbin Avenue, Jinhua 321004, China
Author to whom correspondence should be addressed.
Received: 8 December 2018 / Revised: 29 December 2018 / Accepted: 3 January 2019 / Published: 9 January 2019
(This article belongs to the Special Issue Fabulous Fluorine in Organic and Medicinal Chemistry)
PDF [1131 KB, uploaded 9 January 2019]


The first electrophilic diastereoselective direct introduction of the difluoromethylthio group is described. We used a chiral auxiliary-based approach to illustrate the versatility of our recently developed difluoromethanesulfonyl hypervalent iodonium ylide reagents for the difluoromethylthiolation of indanone-based β-keto esters. Chiral SCF2H-featuring compounds were obtained in up to 93% ee value. View Full-Text
Keywords: fluorine; sulfur; asymmetric synthesis; hypervalent iodine fluorine; sulfur; asymmetric synthesis; hypervalent iodine

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material


Share & Cite This Article

MDPI and ACS Style

Gondo, S.; Matsubara, O.; Chachignon, H.; Sumii, Y.; Cahard, D.; Shibata, N. Asymmetric Electrophilic Difluoromethylthiolation of Indanone-Based β-Keto Esters Using Difluoromethanesulfonyl Hypervalent Iodonium Ylides. Molecules 2019, 24, 221.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top