MacMillan Imidazolidinone OrganoCatalysts™

Chemfiles Volume 6 Article 1

Metal-Free Asymmetric Catalysis

Product Highlights

  • Superior enantiocontrol in numerous transformations
  • High activities at low catalyst loadings
  • Extraordinary functional group tolerance
  • Asymmetric α-fluorination employed in natural product synthesis

MacMillan and co-workers have created chiral imidazolidinone organo-catalysts that function as the linchpin in a variety of directed enantioselective organic reactions, including the enamine-catalyzed α-chlorination and 1,3-dipolar cycloaddition of aldehydes. Sigma‑Aldrich is pleased to offer six imidazolidinone organocatalysts in our collaboration with Materia, Inc. that mediate rapid and enantiocontrolled C–F and C–H bond formation. In the former process, catalyst 1 was utilized in low (5 mol %) loadings in the first example of organocatalytic advanced enantioselective α-fluorination of aldehydes to afford a broad spectrum of highly enantioenriched alcohols.

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  1. (a) MacMillan, D. W. et al. J. Am. Chem. Soc. 2000, 122, 9874. (b) MacMillan, D. W. et al. J. Am. Chem. Soc. 2005, 127, 8826.

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