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.
Highlights
In the field of organofluorine chemistry one of the major present concerns is the development of new methods for the construction of novel chemical scaffolds
In a first series of experiments, we studied the difluoromethylthiolation of β-enamino esters 2a–e prepared from methyl 6-methyl-1-indanone-2- carboxylate methylthiolation of β-enamino esters 2a–e prepared from methyl 6-methyl-1-indanone-2- carboxylate and various chiral amines in order to determine the most appropriate chiral auxiliary (Table 1)
In the presence of 20 mol% of copper difluoromethanesulfonyl hypervalent iodonium ylide 1b reacted in 1,4-dioxane at room temperature bromide, the difluoromethanesulfonyl hypervalent iodonium ylide 1b reacted in 1,4-dioxane at for 5 h followed by acidic cleavage of the resulting imine product to afford the 2-difluoromethylthioroom temperature for 5 h followed by acidic cleavage of the resulting imine product to afford the
Summary
In the field of organofluorine chemistry one of the major present concerns is the development of new methods for the construction of novel chemical scaffolds In this vein, the combination of sulfur, carbon and fluorine atoms has given birth to emergent motifs, which include SCF3 , SCF2 H, SCF2 FG (FG = SO2 Ar, SAr, PO(OR) , COAr, Rf), SCFH2 [1,2,3,4]. The SCF3 chemotype is encountered in several biologically active molecules, albeit virtually absent in marketed drugs. The reason it elicits such enthusiasm is the exceptional high lipophilicity of SCF3 molecules that confers a high potential in medicinal chemistry. The synthesis of enantioenriched molecules featuring a SCF2 R motif directly linked to the chiral center is an issue worth consideration in the context of designing new chiral drugs
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