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Synfacts 2009(12): 1377-1377  
DOI: 10.1055/s-0029-1218250
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

NHC-Catalyzed Enantioselective Synthesis of β-Trifluoromethyl-β-lactones

Contributor(s): Mark Lautens, Chit Tsui
X.-N. Wang, P.-L. Shao, H. Lv, S. Ye*
Institute of Chemistry, Chinese Academy of Sciences, Beijing, P. R. of China
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Publikationsverlauf

Publikationsdatum:
20. November 2009 (online)

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Significance

Trifluoromethyl-substituted compounds and β-lactones are two useful building blocks and important structural motifs in bioactive natural products and pharmaceuticals. The authors describe a highly diastereo- and enantioselective synthesis of β-trifluoromethyl-β-lactones bearing two contiguous stereocenters. The method utilizes a chiral N-heterocyclic carbene (NHC) catalyzed formal cycloaddition reaction of alkyl(aryl)ketenes and trifluoromethyl ketones.