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 inMolecules (Basel, Switzerland) Vol. 24; no. 2; p. 221
Main Authors Gondo, Satoshi, Matsubara, Okiya, Chachignon, Hélène, Sumii, Yuji, Cahard, Dominique, Shibata, Norio
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 09.01.2019
MDPI
Subjects
Chemical Sciences
Chromatography
Organic chemistry
Solvents
United States > US
Japan
hypervalent iodine
sulfur
asymmetric synthesis
fluorine
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ISSN1420-3049
1420-3049
DOI10.3390/molecules24020221

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Summary: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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PMCID: PMC6359606
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24020221