In situ generation of electrophilic trifluoromethylthio reagents for enantioselective trifluoromethylthiolation of oxindoles.
An organocatalytic asymmetric trifluoromethylthiolation reaction via in situ generation of active electrophilic trifluoromethylthio species involving trichloroisocyanuric acid and AgSCF3 as a practical and easily handled electrophilic SCF3 source for CSP(3)-SCF3 bond formation was developed. Reactions with this one-pot version strategy occurred in good yields and excellent stereoselectivities to access enantiopure oxindoles bearing a SCF3-substituted quaternary chiral center. The straightforward process described here makes use of simple starting materials and proceeds under mild conditions, which will be useful in medicinal chemistry and diversity-oriented syntheses.
Department of Chemistry, South University of Science and Technology of China , Shenzhen 518055, P. R. China.
Xing-Li
XL
Zhu
Jin-Hui
JH
Xu
Dao-Juan
DJ
Cheng
Li-Jiao
LJ
Zhao
Xin-Yuan
XY
Liu
Bin
B
Tan
D002384:Catalysis; D018360:Crystallography, X-Ray; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D000078183:Oxindoles; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry*; D014227:Triazines / Q000737:chemistry
D006845:Hydrocarbons, Fluorinated; D007202:Indicators and Reagents; D007211:Indoles; D000078183:Oxindoles; D013457:Sulfur Compounds; D014227:Triazines; C557580:trichloroisocyanuric acid; C022960:2-oxindole