Endo Selective Diels-Alder Reactions of Furan in Ionic Liquids

Ivan  Hemeon; Carolyn  DeAmicis; Hilary  Jenkins; Peter  Scammells; Robert D.  Singer

doi:10.1055/s-2002-34868

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Synlett 2002(11): 1815-1818
DOI: 10.1055/s-2002-34868

LETTER

Endo Selective Diels-Alder Reactions of Furan in Ionic Liquids

Ivan Hemeon^a, Carolyn DeAmicis^a, Hilary Jenkins^a, Peter Scammells^b, Robert D. Singer*^a
^a Department of Chemistry, Saint Mary’s University, Halifax, B3H 3C3 Canada
Fax: +1(902)4205261; e-Mail: robert.singer@stmarys.ca;
^b Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, Victoria, 3052 Australia

Further Information

Publication History

Received 17 April 2002
Publication Date:
21 October 2002 (online)

Abstract
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Abstract

Diels-Alder reactions of the heteroaromatic diene furan proceed with enhanced isolated yields and reversal of endo/exo selectivity (2:1 endo vs exo) in the ionic liquids [bmim]BF₄ and [bmim]PF₆ compared to conventional methods. The potential utility of ionic liquids as solvents in Diels-Alder reactions of thiophene and pyrrole derivatives has also been demonstrated.

Key words

Diels-Alder reactions - heterocycles - solvent effects - furans - pyrroles

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