One-pot three-component reaction of p-quinone monoacetals, l-proline and naphthols to afford N-aryl-2-arylpyrrolidines

Abstract

The one-pot three-component reaction of p-quinone monoacetals (or p-quinol ethers), L-proline and naphthols is developed for the synthesis of N-aryl-2-arylpyrrolidines under mild conditions with high chemo- and regioselectivity. The reaction may involve multiple processes including condensation, decarboxylation and demethoxylation for the the generation of N-arylated 3,4-dihydro-2H-pyrrolium followed by controllable capture by naphthols. In the absence of a naphthol, p-quinone monoacetal coupled with L-proline to form a complex dipyrroloquinoline product.