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

Satoshi Gondo (1) , Okiya Matsubara (1) , Hélène Chachignon (2) , Yuji Sumii (1) , Dominique Cahard (2) , Norio Shibata (1, 3)

1 NIT - Nagoya Institute of Technology
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
3 Zhejiang Normal University

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.

Domaines: Chimie organique

Satoshi Gondo, Okiya Matsubara, Hélène Chachignon, Yuji Sumii, Dominique Cahard, et al.. Asymmetric Electrophilic Difluoromethylthiolation of Indanone-Based β-Keto Esters Using Difluoromethanesulfonyl Hypervalent Iodonium Ylides. Molecules, 2019, 24 (2), pp.221. ⟨10.3390/molecules24020221⟩. ⟨hal-02321615⟩