4.6 Article

Catalytic Asymmetric Synthesis of Enantioenriched Heterocycles Bearing a CCF3 Stereogenic Center

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 24, Pages 8664-8684

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500361

Keywords

asymmetric synthesis; heterocycles; organocatalysts; organometallic catalysis; trifluoromethylation

Funding

  1. National Natural Science Foundation of China [21303128]
  2. Scientific Research Foundation for Returned Scholars [[2013]1792]
  3. Research Fund for the Doctoral Program of Higher Education of China by Ministry of Education of China [20130143120003]
  4. Platform for Drug Discovery, Informatics, and Structural Life Science from MEXT Japan
  5. ACT-C from JST

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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.

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