Intramolecular Diels-Alder reactions of furans with a merely strain-activated tetrasubstituted alkene: Bicyclopropylidene

Tetrahedron

Volumn 52, Issue 37, 1996, Pages 12185-12196

  Heiner, Thomas ^a   Kozhushkov, Sergei I ^a   Noltemeyer, Mathias ^a   Haumann, Thomas ^b   Boese, Roland ^b   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; FURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

BETULACEAE;

EID: 0030576867     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00720-X     Document Type: Article

References (22)

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2. 2. de Meijere, A.; Erden, I.; Weber, W.; Kaufmann, D. J. Org. Chem. 1988, 53, 152, and refs cited therein.
3. 3. Brandi, A.; Goti, A.; Kozhushkov, S. I.; de Meijere, A. J. Chem. Soc., Chem. Commun. 1994, 2185.
4. 4. Bräse, S.; de Meijere, A. Angew. Chem. 1995, 107, 2741; Angew. Chem., Int. Ed. Engl. 1995, 34, 2545.
5. 4. Bräse, S.; de Meijere, A. Angew. Chem. 1995, 107, 2741; Angew. Chem., Int. Ed. Engl. 1995, 34, 2545.
6. 5. Gleiter, R.; Haider, R.; Conia, J.-M.; Barnier, J.-P.; de Meijere, A.; Weber, W. J. Chem. Soc., Chem. Commun. 1979, 130.
7. 6. (a) Oppolzer, W. Angew. Chem. 1977, 89, 10; Angew. Chem., Int. Ed. Engl. 1977, 16, 10.
8. 6. (a) Oppolzer, W. Angew. Chem. 1977, 89, 10; Angew. Chem., Int. Ed. Engl. 1977, 16, 10.
9. (b) Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63.
10. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183.
11. 7. Heiner, T.; Michalski, S.; Gerke, K.; Kuchta, G.; Buback, M.; de Meijere, A. Synlett 1995, 355.
12. 8. (a) Thomas, E. W. Tetrahedron Lett. 1983, 24, 1467.
13. (b) Sternberg, E.; Binger, P. ibid. 1985, 26, 301.
14. 9. de Meijere, A.; Kozhushkov, S. I.; Zefirov, N. S. Synthesis 1993, 681.
15. 10. The presence of HMPA proved to be crucial for the success of this nucleophilic substitution. For a similar observation see: Trost, B. M.; Runge, T. A. J. Am. Chem. Soc. 1981, 103, 7559.
16. 11. Lukin, K. A.; Kozhushkov, S. I.; Andrievsky, A. A.; Ugrak, B. I.; Zefirov, N. S. J. Org. Chem. 1991, 56, 6176.
17. 12. For potential difficulties see also: Stork, G.; Keitz, P. F. Tetrahedron Lett. 1989, 30, 6981.
18. 13. Compound 6 was prepared to test the possibility of using a temporary silicon tether to control the regiochemistry in such a cycloaddition. For this concept of temporary silicon tethers cf. also: Stork, G.; Chan, G. A.; Breault, G. A. J. Am. Chem. Soc. 1992, 114, 7578.
19. 14. The same sensitivity was observed for analogous bicyclic acetals prepared by intramolecular Diels-Alder reactions of 5-methoxyfuran derivatives. See ref 7.
20. 15. Further details of the crystal structure investigations of 7a, 8, 10 are available on request from the Cambridge Crystallographic Data Centre on quoting the names of the authors and the journal citation: CCDC, 12 Union Rd., Cambridge CB2 1EZ, U.K. (Fax: Int. + 1223-336033; E-mail: teched@chemcrys.cam.ac.uk).
21. 16. Lenn, N. D.; Shin, Y.; Stankovic, M. T.; Liu, H. J. Am. Chem. Soc. 1989, 111, 3065.
22. 17. Lai, M.; Liu, L.; Liu, H. J. Am. Chem. Soc. 1991, 113, 7388.