4.8 Article

Highly Enantioselective Copper-Catalyzed Electrophilic Trifluoromethylation of β-Ketoesters

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 26, Pages 10769-10772

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja3039773

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Funding

  1. Alexander von Humboldt Foundation
  2. Deutsche Forschungsgemeinschaft [SFB 623, TP B6]

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Enantioselective Cu-catalyzed trifluoromethylation of beta-ketoesters using commercially available trifluoromethylating reagents is reported. A number of alpha-CF3 beta-ketoesters are obtained with up to 99% ee. The trifluoromethylated products were then transformed diastereoselectively to alpha-CF3 beta-hydroxyesters with two adjacent quaternary stereocenters via a Grignard reaction.

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