1-Naphthyl-TADDOL/Emim BF4: A new catalytic system for the asymmetric addition of Chan's diene to aromatic aldehydes

摘要

A new organocatalytic system was tested as a promoter for the asymmetric addition of Chan's diene to aldehydes under solventfree conditions. This new organocatalyst generated in situ by mixing 1-naphthyl-TADDOL derivative and Emim BF4 was able to give enantioenriched vinylogous aldols and hetero-Diels-Alder cycloadducts. A mechanistic investigation through the detection of nonlinear effects confirmed the involvement of the ionic liquid in the formation of a new catalytic supramolecular species.