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Molecules 2019, 24(2), 221; https://doi.org/10.3390/molecules24020221

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

1
Department of Nanopharmaceutical Sciences, Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan
2
CNRS, UMR 6014 COBRA, Normandie Université, 1 Rue Tesnière, F-76821 Mont-Saint-Aignan Cedex, France
3
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)
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Abstract

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
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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).

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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.

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