Inter- and intramolecular Diels-Alder/retro-Diels-Alder reactions of4-silylated oxazoles

Arkivoc

Volumn 2002, Issue 6, 2002, Pages 22-34

  Ducept, Pascal C ^a   Marsden, Stephen P ^a,b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

Diazoacetate; Diels Alder; Furans; Retro Diels Alder; Silylated oxazoles

Indexed keywords

2 ETHOXY 3 METHOXYCARBONYL 5 PHENYLFURAN; 2 ETHOXY 3 METHOXYCARBONYL 6,7 DIHYDRO 5H BENZOFURAN 4 ONE; 2 ETHOXY 3 TRIMETHYLSILYL 6,7 DIHYDRO 5H BENZOFURAN 4 ONE; 2 ETHOXY 3,4 DIMETHOXYCARBONYL 5 (2 THIOPHENYL)FURAN; 2 ETHOXY 3,4 DIMETHOXYCARBONYL 5 METHYLFURAN; 2 ETHOXY 3,4 DIMETHOXYCARBONYL 5 PHENYLFURAN; 2 ETHOXY 3,4,5 TRIMETHOXYCARBONYLFURAN; 2 ETHOXY 5 ETHYL 3 METHOXYCARBONYLFURAN; 5 ETHOXY 2 (4 OXO 6 METHOXYCARBONYLHEX 5 YNYL) 4 TRIETHYLSILYLOXAZOLE; 5 ETHOXY 2 (4 OXO 6 TRIMETHYLSILYLHEX 5 YNYL) 4 TRIETHYLSILYLOXAZOLE; ACETIC ACID DERIVATIVE; ALKYNE DERIVATIVE; AZO COMPOUND; FURAN DERIVATIVE; NITRILE; OXAZOLE DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DIELS ALDER REACTION; POLYMERIZATION; SILYLATION;

EID: 3242789315     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (16)

1. For reviews of Diels-Alder reactions of oxazoles, see: (a) Boger, D. L. Tetrahedron 1983, 39, 2869.
2. (b) Boger, D. L. Chem. Rev. 1986, 86, 781.
3. (c) Hassner, A.; Fischer, B. Heterocycles, 1993, 35, 1441.
4. See, for example: Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 2000, 122, 4295 and references therein.
5. Huisgen, R.; König, H.; Binsch, G.; Sturm, H. J. Angew. Chem. 1961, 73, 368.
6. Connell, R.; Scavo, F.; Helquist, P.; Åkermark, B. Tetrahedron Lett. 1986, 27, 5559.
7. Doyle, K. J.; Moody, C. J. Tetrahedron 1994, 50, 3761.
8. Shankar, B. K. R.; Schechter, H. Tetrahedron Lett. 1982, 23, 2277.
9. Dewar, M. J. S.; Turchi, I. J. Chem. Rev., 1975, 75, 724.
10. (a) Johnsen, B. A.; Undheim, K. Acta. Chem. Scand., Ser. B 1983, 37, 127.
11. (b) Shimada, S.; Maeda, H. Chem. Pharm. Bull. 1983, 3460.
12. Ducept, P. C.; Marsden, S. P. Synlett 2000, 692.
13. Boyd, G. V. "Oxazoles and their benzo derivatives", in Comprehensive Heterocyclic Chemistry, A. R. Katritzky; C. W. Rees eds., Pergamon, Oxford, vol. 5, chapter 4.18.
14. Nyström, J.-E.; McCanna, T. D.; Helquist, P.; Amoroux, R. Synthesis 1988, 56.
15. Midland, M.; Tramontano, A; Cable, J. R. J. Org. Chem. 1980, 45, 28
16. Crandall, J. K.; Michaely, W. J. J. Org. Chem. 1984, 49, 4244.