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

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

Abstract

All articles of this category

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

Full Text

References

1 Hutchinson SA. Baker SP. Scammells PJ. Bioorg. Med. Chem. Lett. 1999, 9: 933

2 Brion F. Tetrahedron Lett. 1982, 23: 5299

3 Nelson WL. Allen DR. J. Heterocycl. Chem. 1972, 9: 561

4a Dauben WG. Krabbenhoft HO. J. Am. Chem. Soc. 1976, 98: 1992

4b Kotsuki H. Nishizawa H. Ochi M. Matsuoka K. Bull. Chem. Soc. Jpn. 1982, 55: 496

5 . Murthy YVS. Pillai CN. Synth. Commun. 1991, 21: 783

6a Wasserscheid P. Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772

6b Welton T. Chem. Rev. 1999, 99: 2071

6c Holbrey JD. Seddon KR. Clean Products and Processes 1999, 1: 223

7a Earle MJ. McCormac PB. Seddon KR. Green Chem. 1999, 1: 23

7b Fischer T. Sethi T. Welton T. Woolf J. Tetrahedron Lett. 1999, 40: 793

7c Lee CW. Tetrahedron Lett. 1999, 40: 2461

7d Song CE. Shim WH. Roh EJ. Lee S. Choi JH. Chem. Commun. 2001, 1122

7e Zulfiqar F. Kitazume T. Green Chem. 2000, 2: 137

7f Howarth J. Hanlon K. Fayne D. McCormac P. Tetrahedron Lett. 1997, 38: 3097

8 Huddleston JG. Visser AE. Reichert WM. Willauer HD. Broker GA. Rogers RD. Green Chem. 2001, 3: 156

9 Moore JA. Emmett PM. J. Org. Chem. 1983, 48: 1105

10 Lee MW. Herndon WC. J. Org. Chem. 1978, 43: 518

11 Helder R. Wynberg H. Tetrahedron Lett. 1972, 13: 605

12 Prinzbach H. Fuchs R. Kitzing R. Angew. Chem., Int. Ed. Engl. 1968, 7: 67

13 It has been reported that mono Diels-Alder adducts of this type undergo further Diels-Alder reaction with diene remaining in the system, see: McCulloch AW. Smith DG. McInnes AG. Can. J. Chem. 1973, 51: 4125

14 Acheson RM. J. Chem. Soc. 1961, 457