Journal
CHEM
Volume 5, Issue 11, Pages 2987-2999Publisher
CELL PRESS
DOI: 10.1016/j.chempr.2019.09.012
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Funding
- National Natural Science Foundation of China [21425208, 21790362, 21702225, 21421002]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- SIOC
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Despite the impressive progress recently made in transition-metal-catalyzed fluoroalkylation, the related asymmetric fluoroalkylation remains a challenging topic. Here, we report a copper-catalyzed highly enantioselective difluoroalkylation of secondary propargyl sulfonates using difluoroenoxysilanes. The reaction proceeds under mild reaction conditions with Cu(I)/PyBox as the catalyst. The advantages of this method include high efficiency, high enantioselectivity (enantiomeric ratio up to 99:1), and excellent functional-group tolerance. The resulting chiral propargylic alpha,alpha-difluoroketones can be transformed into enantiomerically enriched propargyl difluoromethylated compounds, providing a good platform for accessing a wide range of chiral difluoromethylated compounds that are of great interest in medicinal chemistry and materials science.
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