Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 12, Pages 3187-3191Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201711463
Keywords
asymmetric catalysis; copper; difluoroalkylation; propargyl sulfonates; trifluoromethylation
Categories
Funding
- National Natural Science Foundation of China [21425208, 21672238, 21702225, 21332010, 21421002]
- National Basic Research Program of China (973 Program) [2015CB931900]
- Chinese Academy of Sciences [XDB20000000]
- SIOC
Ask authors/readers for more resources
It is challenging to stereoselectively introduce a trifluoromethyl group (CF3) into organic molecules. To date, only limited strategies involving direct asymmetric trifluoromethylation have been reported. Herein, we describe a new strategy for direct asymmetric trifluoromethylation through the copper-catalyzed stereospecific trifluoromethylation of optically active secondary propargyl sulfonates. The reaction enables propargylic trifluoromethylation with high regioselectivity and stereoselectivity. The reaction could also be extended to stereospecific propargylic difluoroalkylation. Transformations of the resulting enantiomerically enriched fluoroalkylated alkynes led to a variety of chiral fluoroalkylated compounds, thus providing a useful protocol for applications in the synthesis of fluorinated complexes.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available