Catalytic asymmetric synthesis of enantioenriched heterocycles bearing a C-CF3 stereogenic center.
Given the important agricultural and medicinal application of optically pure heterocycles bearing a trifluoromethyl group at the stereogenic carbon center in the heterocyclic framework, the exploration of efficient and practical synthetic strategies to such types of molecules remains highly desirable. Catalytic enantioselective synthesis has one clear advantage that it is more cost-effective than other synthetic methods, but remains limited by challenges in achieving excellent yield and stereoselectivities with a low catalyst loading. Thus far, numerous models of organo- and organometal-catalyzed asymmetric reactions have been exploited to achieve this elusive goal over the past decade. This review article describes recent progress on this research topic, and focuses on an understanding of the catalytic asymmetric protocols exemplified in the catalytic enantioselective synthesis of a wide range of complex enantioenriched trifluoromethylated heterocycles.
Department of Chemistry, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan 430070 (P.R. China). huangyy@whut.edu.cn.
Yi-Yong
YY
Huang
Department of Chemistry, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan 430070 (P.R. China).
Xing
X
Yang
Department of Chemistry, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan 430070 (P.R. China).
Zhuo
Z
Chen
Department of Chemistry, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan 430070 (P.R. China).
Francis
F
Verpoort
Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan), Fax: (+81) 52-735-5442. nozshiba@nitech.ac.jp.
Norio
N
Shibata
D000147:Acids, Heterocyclic / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism
D000147:Acids, Heterocyclic
asymmetric synthesis; heterocycles; organocatalysts; organometallic catalysis; trifluoromethylation