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Synfacts 2011(12): 1317-1317  
DOI: 10.1055/s-0031-1289335
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Fluorination of Epoxides via Cooperative Catalysis

Contributor(s): Mark Lautens, Lei Zhang
J. A. Karlow, A. G. Doyle*
Princeton University, USA
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Publication History

Publication Date:
18 November 2011 (online)

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Significance

Following the authors’ first report on enantioselective fluorination of epoxides (J. Am. Chem. Soc. 2010, 132, 3268; Synfacts 2010, 673), a detailed mechanistic study was performed. The elucidation of a bimetallic mechanism for the enantio-­discriminating epoxide-opening step allowed significant improvement in catalyst design, rate, yield, and ee.