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

✍ Scribed by Villano, Rosaria ;Acocella, Maria ;Sio, Vincenzo ;Scettri, Arrigo

• Book ID: 111488159
• Publisher: Walter de Gruyter GmbH
• Year: 2010
• Tongue: English
• Weight: 596 KB
• Volume: 8
• Category: Article
• ISSN: 2391-5420
• DOI: 10.2478/s11532-010-0100-5

✦ Synopsis

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 BF 4 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.