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Chiral Phosphoric Acid Catalyzed Asymmetric Desymmetrization of -Quinamines with Isocyanates: Access to Functionalized Imidazolidin-2-one Derivatives. | LitMetric

AI Article Synopsis

  • A new method for selectively transforming -quinamines into functionalized imidazolidin-2-one derivatives using isocyanates has been developed, utilizing chiral phosphoric acid as a catalyst.
  • This process yields high-quality products under mild conditions and can be executed on a larger scale with low catalyst amounts.
  • The resulting chiral compounds can be easily converted into other valuable structures while maintaining their enantiopurity, showcasing the method's practical applications in synthesis.

Article Abstract

The development of enantioselective desymmetrization of -quinamines with isocyanates catalyzed by chiral phosphoric acid is reported. The strategy provides concise access to functionalized imidazolidin-2-one derivatives in high yields and enantioselectivities under mild reaction conditions. Remarkably, this reaction could be performed on a gram scale using 5 mol % catalyst loading and the chiral imidazolidin-2-one derivatives could be easily transformed into valuable scaffolds without disturbing the enantiopurity, demonstrating the synthetic utility of this protocol.

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Source
http://dx.doi.org/10.1021/acs.orglett.1c02889DOI Listing

Publication Analysis

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