Asymmetric Electrophilic Difluoromethylthiolation of Indanone-Based β-Keto Esters Using Difluoromethanesulfonyl Hypervalent Iodonium Ylides
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...
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| Published in | Molecules (Basel, Switzerland) Vol. 24; no. 2; p. 221 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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MDPI AG
09.01.2019
MDPI |
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| ISSN | 1420-3049 1420-3049 |
| DOI | 10.3390/molecules24020221 |
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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. |
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| AbstractList | 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 SCF
2
H-featuring compounds were obtained in up to 93% ee value. 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. 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.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. 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. |
| Author | Matsubara, Okiya Shibata, Norio Chachignon, Hélène Sumii, Yuji Gondo, Satoshi Cahard, Dominique |
| AuthorAffiliation | 2 CNRS, UMR 6014 COBRA, Normandie Université, 1 Rue Tesnière, F-76821 Mont-Saint-Aignan Cedex, France; helene.chachignon@insa-rouen.fr (H.C.); dominique.cahard@univ-rouen.fr (D.C.) 3 Institute of Advanced Fluorine-Containing Materials, Zhejiang Normal University, 688 Yingbin Avenue, Jinhua 321004, China 1 Department of Nanopharmaceutical Sciences, Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan; 29411074@stn.nitech.ac.jp (S.G.); cjh11141@nitech.jp (O.M.); sumii.yuji@nitech.ac.jp (Y.S.) |
| AuthorAffiliation_xml | – name: 3 Institute of Advanced Fluorine-Containing Materials, Zhejiang Normal University, 688 Yingbin Avenue, Jinhua 321004, China – name: 1 Department of Nanopharmaceutical Sciences, Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan; 29411074@stn.nitech.ac.jp (S.G.); cjh11141@nitech.jp (O.M.); sumii.yuji@nitech.ac.jp (Y.S.) – name: 2 CNRS, UMR 6014 COBRA, Normandie Université, 1 Rue Tesnière, F-76821 Mont-Saint-Aignan Cedex, France; helene.chachignon@insa-rouen.fr (H.C.); dominique.cahard@univ-rouen.fr (D.C.) |
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| CitedBy_id | crossref_primary_10_6023_cjoc202006021 crossref_primary_10_1016_j_jfluchem_2020_109652 crossref_primary_10_1002_anie_202210509 crossref_primary_10_1021_acs_orglett_2c03017 crossref_primary_10_1002_ange_202210509 crossref_primary_10_1021_jacs_4c12093 crossref_primary_10_1002_cjoc_201900298 |
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| Copyright | 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. Distributed under a Creative Commons Attribution 4.0 International License 2019 by the authors. 2019 |
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| Title | Asymmetric Electrophilic Difluoromethylthiolation of Indanone-Based β-Keto Esters Using Difluoromethanesulfonyl Hypervalent Iodonium Ylides |
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