Organocatalysis is becoming an increasing important tool for asymmetric synthesis. However, high catalyst loading (up to 20 mol%) and difficulty for catalyst recovery are the major drawbacks of organocatalysis, which make organocatalyst recycling highly desirable. Organofluorine is an active topic in current medicinal and agricultural chemistry. Three cinchona alkaloid-based fluorous organocatalysts for asymmetric synthesis are introduced in this poster. The attachment of fluorocarbon chain to these organocatalysts can facilitate their recovery by fluorous solid-phase extraction (F-SPE) technique. These recyclable fluorous organocatalysts have been successfully applied for the Michael addition of maleimides/nitroolefins and β-ketoesters to form a fluorinated quaternary carbon center adjacent to another chiral center; for Robinson annulation of fluorinated β-ketoesters and chalchone; for fluorination of β-ketoesters; for organocatalytic Michael/Michael/aldol and Michael/aza-Henry/lactamization domino reactions to form highly functionalized cyclohexanes of six chiral centers and fluorinated 2-piperidinones respectively. These organocatalytic reactions have high yield and enantioselectivity.

Recyclable organocatalysis for asymmetric synthesis of organofluorine compounds

250th National Meeting (2015)

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