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

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 ?-keto esters. Chiral SCF?H-featuring compounds were obtained in up to 93% ee value.

SUBMITTER: Gondo S

PROVIDER: S-EPMC6359606 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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

Gondo Satoshi S Matsubara Okiya O Chachignon Hélène H Sumii Yuji Y Cahard Dominique D Shibata Norio N

Molecules (Basel, Switzerland) 20190109 2

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. ...[more]

PMID: 30634428

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