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

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Villano R., Acocella M., Sio V., Scettri A.
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A new organocatalytic system was tested as a promoter for the asymmetric addition of Chan’s diene to aldehydes under solvent-free 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.
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