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Amide‐phosphonium Salt Catalyzed Enantioselective Vinylogous Mannich Addition of Coumarins to Isatin Imines

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An asymmetric vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines catalysed by amide phosphonium salt is described. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and… Click to show full abstract

An asymmetric vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines catalysed by amide phosphonium salt is described. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantioselectivities. The utility of this method was illustrated by a gram scale synthesis using as low as 0.1 mol % of catalyst without chromatographic purification, and removal of the Boc protecting groups on the primary amine functionality in Mannich products.

Keywords: isatin imines; amide phosphonium; salt catalyzed; vinylogous mannich; phosphonium salt

Journal Title: ChemCatChem
Year Published: 2019

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