Fructose-derived ionic liquids: Recyclable homogeneous supports

Tetrahedron Letters

Volumn 44, Issue 46, 2003, Pages 8399-8402

  Handy, Scott T ^a   Okello, Maurice ^a  

^a BINGHAMTON UNIVERSITY   (United States)

Author keywords

Carbene; Diels Alder reaction; Ionic liquid; Soluble support; Transesterification

Indexed keywords

FRUCTOSE; IMIDAZOLE DERIVATIVE;

ARTICLE; DIELS ALDER REACTION; LIQUID; RECYCLING; TRANSESTERIFICATION;

BETULACEAE;

EID: 0141991233     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.121     Document Type: Article

References (23)

1. Handy S.T., Okello M., Dickenson G. Org. Lett. 5:2003;2513-2515.
2. Handy S.T. Chem. Eur. J. 9:2003;2938-2944.
3. Handy S.T., Okello M. Tetrahedron Lett. 44:2003;8395.
4. For recent reviews on ionic liquids, see: Welton, T. Chem. Rev. 1999, 99, 2071-2083; Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789; Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692; Ionic Liquids in Synthesis; Wassercheid, P.; Welton, T., Eds.; Wiley-VCH: Weinheim, 2003.
5. For recent reviews on ionic liquids, see: Welton, T. Chem. Rev. 1999, 99, 2071-2083; Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789; Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692; Ionic Liquids in Synthesis; Wassercheid, P.; Welton, T., Eds.; Wiley-VCH: Weinheim, 2003.
6. For recent reviews on ionic liquids, see: Welton, T. Chem. Rev. 1999, 99, 2071-2083; Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789; Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692; Ionic Liquids in Synthesis; Wassercheid, P.; Welton, T., Eds.; Wiley-VCH: Weinheim, 2003.
7. For recent reviews on ionic liquids, see: Welton, T. Chem. Rev. 1999, 99, 2071-2083; Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789; Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692; Ionic Liquids in Synthesis; Wassercheid, P.; Welton, T., Eds.; Wiley-VCH: Weinheim, 2003.
8. For a review, see: Fruechtel J.S., Jung G. Angew. Chem., Int. Ed. Engl. 35:1996;17-42.
9. For reviews, see: Spanka, C.; Wentworth, P., Jr.; Janda, K. D. Combinatorial Chemistry & High Throughput Screening 2002, 5, 233-240; Dickerson, T. J.; Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325-3343.
10. For reviews, see: Spanka, C.; Wentworth, P., Jr.; Janda, K. D. Combinatorial Chemistry & High Throughput Screening 2002, 5, 233-240; Dickerson, T. J.; Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325-3343.
11. For a report focusing on methods to increase the loading of these supports, see: Sunder A., Heinemann J., Frey H. Chem. Eur. J. 6:2000;2499-2506.
12. For selected studies, see: Huddleston, J. G; Visser, A. E.; Reichert, W. M.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Green Chem. 2001, 3, 156-164; Golding, J.; Forsyth, S.; MacFarlane, D. R.; Forsyth, M.; Deason, G. B. Green Chem. 2002, 4, 223-229; MacFarlane, D. R.; Forsyth, S. A.; Golding, J.; Deacon, G. B. Green Chem. 2002, 4, 444-448; Holbrey, J. D.; Reichert, W. M.; Swatloski, R. P.; Broker, G. A.; Pitner, W. R.; Seddon, K. R.; Rogers, R. D. Green Chem. 2002, 4, 407-413.
13. For selected studies, see: Huddleston, J. G; Visser, A. E.; Reichert, W. M.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Green Chem. 2001, 3, 156-164; Golding, J.; Forsyth, S.; MacFarlane, D. R.; Forsyth, M.; Deason, G. B. Green Chem. 2002, 4, 223-229; MacFarlane, D. R.; Forsyth, S. A.; Golding, J.; Deacon, G. B. Green Chem. 2002, 4, 444-448; Holbrey, J. D.; Reichert, W. M.; Swatloski, R. P.; Broker, G. A.; Pitner, W. R.; Seddon, K. R.; Rogers, R. D. Green Chem. 2002, 4, 407-413.
14. For selected studies, see: Huddleston, J. G; Visser, A. E.; Reichert, W. M.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Green Chem. 2001, 3, 156-164; Golding, J.; Forsyth, S.; MacFarlane, D. R.; Forsyth, M.; Deason, G. B. Green Chem. 2002, 4, 223-229; MacFarlane, D. R.; Forsyth, S. A.; Golding, J.; Deacon, G. B. Green Chem. 2002, 4, 444-448; Holbrey, J. D.; Reichert, W. M.; Swatloski, R. P.; Broker, G. A.; Pitner, W. R.; Seddon, K. R.; Rogers, R. D. Green Chem. 2002, 4, 407-413.
15. For selected studies, see: Huddleston, J. G; Visser, A. E.; Reichert, W. M.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Green Chem. 2001, 3, 156-164; Golding, J.; Forsyth, S.; MacFarlane, D. R.; Forsyth, M.; Deason, G. B. Green Chem. 2002, 4, 223-229; MacFarlane, D. R.; Forsyth, S. A.; Golding, J.; Deacon, G. B. Green Chem. 2002, 4, 444-448; Holbrey, J. D.; Reichert, W. M.; Swatloski, R. P.; Broker, G. A.; Pitner, W. R.; Seddon, K. R.; Rogers, R. D. Green Chem. 2002, 4, 407-413.
16. There has already been a single report exploring the use of a RTIL as a soluble support, see: Fraga-Dubreuil J., Bazureau J.P. Tetrahedron Lett. 42:2001;6097-6100.
17. Aggarwal V.K., Emme I., Mereu A. Chem. Commun. 2002;1612-1613.
18. 1H NMR) of acrylate 2 . The method of quenching this reaction was quite important, since unless all of the amine hydrochloride by-product was neutralized prior to extraction and concentration, significant amounts (up to 20%) of the hydrogen chloride addition product 3 were obtained.
19. All crude Diels-Alder adducts displayed spectral properties consistent with those reported in the literature.
20. General procedure for the Diels-Alder reaction: In a pressure tube with 0.2688 g (0.5339 mmol) of acrylate 2 was added 1.0 mg (0.0053 mmol) of hydroquinone and 0.5 mL (5 mmol) of 2,3-dimethylbutadiene. The mixture was purged with argon, then sealed and heated in an oil bath to 120°C. After 12 h, the tube was cooled to room temperature and the excess diene and any volatile by-products removed by concentration in vacuo. The crude product was the triturated with cyclohexane (2×10 mL) and any residual cyclohexane was removed from the supported product in vacuo to afford the Diels-Alder adduct ready for cleavage from the support.
21. Herzig J., Nudelman A., Gottlieb H.E., Fischer B. J. Org. Chem. 51:1986;727-730.
22. General procedure for transesterification: the supported Diels-Alder adduct with 2,3-dimethylbutadiene (crude, 0.5339 mmol) was dissolved in 5 mL of methanol. To this solution was added 17 mg (0.2668 mmol) of potassium cyanide and the reaction was stirred 12 h. The methanol was removed in vacuo and the remaining residue was triturated with cyclohexane (3×10 mL). The combined cyclohexane washes were concentrated in vacuo to afford 0.60 g (63% isolated over three steps) of methyl 1,2-dimethylcyclohexene-4-carboxylate.
23. The modest yields of the Diels-Alder adducts over this three step sequence are most likely due to the volatility of the methyl esters, since the yield for the less volatile benzyl ester is much higher.