Villano, Rosaria and Acocella, Maria Rosaria and De Sio, Vincenzo and Scettri, Arrigo (2010) 1-Naphthyl-TADDOL/Emim BF4: a new catalytic system for the asymmetric addition of Chan’s diene to aromatic aldehydes. Central European Journal of Chemistry, Vol. 8 (6), p. 1172-1178. ISSN 1895-1066. eISSN 1644-3624. Article.
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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.
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