1150634-50-6Relevant articles and documents
Catalytic asymmetric trifluoromethylthiolation via enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides
Zhang, Zhikun,Sheng, Zhe,Yu, Weizhi,Wu, Guojiao,Zhang, Rui,Chu, Wen-Dao,Zhang, Yan,Wang, Jianbo
, p. 970 - 976 (2017)
The trifluoromethylthio (SCF 3) functional group has been of increasing importance in drug design and development as a consequence of its unique electronic properties and high stability coupled with its high lipophilicity. As a result, methods to introduce this highly electronegative functional group have attracted considerable attention in recent years. Although significant progress has been made in the introduction of SCF 3 functionality into a variety of molecules, there remain significant challenges regarding the enantioselective synthesis of SCF 3 -containing compounds. Here, an asymmetric trifluoromethylthiolation that proceeds through the enantioselective [2,3]-sigmatropic rearrangement of a sulfonium ylide generated from a metal carbene and sulfide (Doyle-Kirmse reaction) has been developed using chiral Rh(II) and Cu(I) catalysts. This transformation features mild reaction conditions and excellent enantioselectivities (up to 98% yield and 98% e.e.), thus providing a unique, highly efficient and enantioselective method for the construction of C(sp 3)-SCF 3 bonds bearing chiral centres.
