Synthesis of 2-benzyloxy-8-oxabicyclo[3.2.1]Oct-6-EN-3-one by [4+3] cycloaddition

Organic Syntheses

Volumn 83, Issue , 2006, Pages 61-69

  Vidal Pascual, María ^b   Martínez Lamenca, Carolina ^b   Hoffmann, H M R ^a   Long, Timothy E ^b   Miller, Marvin J ^b  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85026868536     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.083.0061     Document Type: Article

References (27)

1. a) Hoffmann, H. M. R. Angew. Chem. Int. Ed. Engl. 1984, 23, 1-19;
2. b) Sarhan, A. A. O. Curr. Org. Chem. 2001, 5, 827-844;
3. c) Rigby, J. H.; Pigge, F. C. Org. React. 1997, 51, 351-478.
4. a) Ashcroft, M. R.; Hoffmann, H. M. R. Org. Synth. Coll. Vol. VI, 512;
5. b) Lautens, M.; Bouchain, G. Org. Synth. 2002, 79, 251.
6. Oh, J.; Ziani-Cherif, C.; Choi, J. -R.; Cha, J. K. Org. Synth. 2002, 78, 212.
7. Albizati, K. F.; Murray, D. H. Tetrahedron Lett. 1990, 31, 4109;
8. for the use of Lewis acids and 3-alkoxy-2-oxo-3-alkenenitriles in cycloadditions to cyclopentadiene see Hoffmann, H. M. R.; Giesel, K.; Lies, R.; Ismail, Z.M. Synthesis 1986, 548;
9. see also Niess, B.; Hoffmann, H.M.R. Angew.Chem.Int.Ed. 2005, 44, 26.
10. a) Proemmel, S.; Wartchow, R.; Hoffmann, H. M. R. Tetrahedron 2002, 31, 6199;
11. b) Vidal-Pascual, M.; Proemmel, S.; Beil, W.; Wartchow, R.; Hoffmann, H. M. R. Org. Lett. 2004, 6, 4155.
12. a) Stark, C. B. W.; Eggert, U.; Hoffmann, H. M. R. Angew. Chem. Int. Ed. Engl. 1998, 37, 1266;
13. b) Stark, C. B. W.; Pierau, S.; Wartchow, R.; Hoffmann, H. M. R. Chem. Eur. J. 2000, 6, 684;
14. c) Beck, H.; Stark, C. B. W.; Hoffmann, H. M. R. Org. Lett. 2000, 2, 883.
15. Hoffmann, H. M. R.; Dunkel, R.; Mentzel, M.; Reuter, H.; Stark, C. B. W. Chem. Eur. J. 2001, 7, 4771;
16. Hartung, I. V.; Hoffmann, H. M. R. Angew. Chem. Int. Ed. 2004, 43, 1934.
17. Murray, R. W.; Singh, M. Org. Synth. Coll. Vol. 9, 288.
18. Gaertzen, O.; Misske, A. M.; Wolbers, P.; Hoffmann, H. M. R. Tetrahedron Lett. 1999, 40, 6359;
19. Gaertzen, O.; Misske, A. M.; Wolbers, P.; Hoffmann, H. M. R. Synlett. 1999, 1041;
20. Dunkel, R.; Hoffmann, H. M. R. Tetrahedron 1999, 55, 8385.
21. Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675.
22. Lautens, M.; Stammers, T. A. Synthesis 2002, 1993 and references therein.
23. Harmata, M. Acc. Chem. Res. 2001, 34, 595;
24. Harmata, M.; Rashatasakhon, P. Tetrahedron 2003, 59, 2379.
25. Usher, L. C.; Estrella-Jiménez, M.; Ghiviriga, I.; Wright, D. L. Angew. Chem. Int. Ed. 2002, 41, 4560.
26. Gillingham, D. G.; Kataoka, O.; Garber, S. B.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 12288.
27. Högermeier, J.; Reissig, H.-U.; Brüdgam, I.; Hartl, H. Adv. Synth. Catal. 2004, 346, 1868.