Catalytic asymmetric trifluoromethylthiolation via enantioselective   [2,3]-sigmatropic rearrangement of sulfonium ylides

CORC > 北京大学 > 化学与分子工程学院

	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
刊名	NATURE CHEMISTRY
	2017
关键词	2,3 SIGMATROPIC REARRANGEMENT ALLYL ARYL SULFIDES C-H ACTIVATION DONOR/ACCEPTOR CARBENOIDS BOND FORMATION METAL CARBENE TANDEM YLIDE SULFUR GENERATION COMPLEXES
英文摘要	The trifluoromethylthio (SCF3) 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 SCF3 functionality into a variety of molecules, there remain significant challenges regarding the enantioselective synthesis of SCF3-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))-SCF3 bonds bearing chiral centres.; National Basic Research Program of China (973 programme) [2015CB856600]; Natural Science Foundation of China [21332002]; SCI(E); ARTICLE; 10; 970-976; 9
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/470629]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Zhang, Zhikun,Sheng, Zhe,Yu, Weizhi,et al. Catalytic asymmetric trifluoromethylthiolation via enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides[J]. NATURE CHEMISTRY,2017.
APA	Zhang, Zhikun.,Sheng, Zhe.,Yu, Weizhi.,Wu, Guojiao.,Zhang, Rui.,...&Wang, Jianbo.(2017).Catalytic asymmetric trifluoromethylthiolation via enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides.NATURE CHEMISTRY.
MLA	Zhang, Zhikun,et al."Catalytic asymmetric trifluoromethylthiolation via enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides".NATURE CHEMISTRY (2017).