1,3-Cycloaddition of nitrile oxides in ionic liquids. An easier route to 3-carboxy isoxazolines, potential constrained glutamic acid analogues

Tetrahedron Letters

Volumn 44, Issue 28, 2003, Pages 5327-5330

  Conti, Dario ^a   Rodriquez, Manuela ^a   Sega, Alessandro ^a   Taddei, Maurizio ^a  

^a UNIVERSITY OF SIENA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 BUTYL 3 METHYLIMIDAZOLIUM HEXAFLUOROPHOSPHATE; 1 BUTYL 3 METHYLIMIDAZOLIUM TETRAFLUOROBORATE; ALKENE; CARBOETHOXYFORMONITRILE OXIDE; GLUTAMIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; ION; ISOXAZOLINE DERIVATIVE; NITRILE; OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; DRUG SYNTHESIS; LIQUID;

EID: 0038007832     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01195-X     Document Type: Article

References (17)

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10. For alternative approaches to this kind of nitrile oxide, see: Maiti, D.; Bhattacharya, P. K. Synlett 1998, 385; Kiegiel, J.; Poplawska, M.; Józwik, J.; Kosior, M.; Jurezak, J. Tetrahedron Lett. 1999, 40, 5605; Matt, C.; Gissot, A.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 1191.
11. For alternative approaches to this kind of nitrile oxide, see: Maiti, D.; Bhattacharya, P. K. Synlett 1998, 385; Kiegiel, J.; Poplawska, M.; Józwik, J.; Kosior, M.; Jurezak, J. Tetrahedron Lett. 1999, 40, 5605; Matt, C.; Gissot, A.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 1191.
12. For alternative approaches to this kind of nitrile oxide, see: Maiti, D.; Bhattacharya, P. K. Synlett 1998, 385; Kiegiel, J.; Poplawska, M.; Józwik, J.; Kosior, M.; Jurezak, J. Tetrahedron Lett. 1999, 40, 5605; Matt, C.; Gissot, A.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 1191.
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14. 6]: butyl metylimidazolium terafluoborate and hexafluorophosphate were prepared following: Dupont, J.; Consorti, C.; Suarez, P. A. Z.; de Souza, R. F. Org. Synth 2002, 79, 236. For a recent review on the applications of ionic liquids in organic synthesis, see: Zhao, H.; Malhotra, S. V. Aldrichim. Acta 2002, 35, 75.
15. 6]: butyl metylimidazolium terafluoborate and hexafluorophosphate were prepared following: Dupont, J.; Consorti, C.; Suarez, P. A. Z.; de Souza, R. F. Org. Synth 2002, 79, 236. For a recent review on the applications of ionic liquids in organic synthesis, see: Zhao, H.; Malhotra, S. V. Aldrichim. Acta 2002, 35, 75.
16. In some cases the formation of furoxane 4 could not be prevented, thus yields were lower. Nevertheless, as furoxane remained preferentially in the ionic liquid, the products could be isolated pure without chromatography.
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