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

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

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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DOI: 10.2478/s11532-010-0100-5

Abstract

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.

Item Type:	Article
ID Code:	6141
Status:	Published
Refereed:	Yes
Uncontrolled Keywords:	Organocatalysis, Hydrogen bonding, Chan’s diene, aldol reaction, cycloadditioncatalysis
Subjects:	Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:	002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:	Versita, co-published with Springer-Verlag GmbH
ISSN:	1895-1066
eISSN:	1644-3624
Copyright Holders:	© Versita Sp. z o.o.
Deposited On:	10 Jun 2011 13:38

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