A repetitive approach to the synthesis of medium and large ring compounds with a ring-opening/ring-Closure cascade reaction of siloxycyclopropane derivatives as crucial step

European Journal of Organic Chemistry

Volumn , Issue 11, 1998, Pages 2541-2549

  Ullmann, Astrid ^a   Reißig, Hans Ulrich ^a   Rademacher, Otto ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

2 Siloxycyclopropanecarboxylates; Alkylations; Cesium fluoride; Intramolecular Michael addition; Large ring compounds

Indexed keywords

EID: 2842568417     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199811)1998:11<2541::aid-ejoc2541>3.0.co;2-%23     Document Type: Article

References (25)

1. A. Ullmann, Dissertation, Technische Universität Dresden, 1998.
2. [2a] A. Ullmann, J. Schnaubelt, H.-U. Reißig, Synthesis 1998, 1052-1066.
3. [2b] J. Schnaubelt, A. Ullmann, H.-U. Reißig, Synlett 1995, 1223-1225.
4. P. Deslongchamps, S. Lamothe, H.-S. Lin, Can J. Chem. 1984, 62, 2395-2398.
5. [3b] P. Deslongchamps, B. L. Roy, Can. J. Chem. 1986, 64, 2068-2075.
6. [4a] I. Böhm, E. Hirsch, H.-U. Reißig, Angew: Chem. 1981, 93, 593-594; Angew. Chem. Int. Ed. Engl. 1981, 20, 574.
7. [4a] I. Böhm, E. Hirsch, H.-U. Reißig, Angew: Chem. 1981, 93, 593-594; Angew. Chem. Int. Ed. Engl. 1981, 20, 574.
8. [4b] I. Reichelt, H.-U. Reißig, Liebigs Ann. Chem. 1984, 531-551.
9. [4c] Review: H.-U. Reißig, Top. Curr. Chem. 1988, 144, 73-135.
10. [5a] Review: K. Ziegler in Houben-Weyl, vol. 4/2, 4th ed. (Ed.: E. Müller), Thieme, Stuttgart, 1955, p. 729-822.
11. [5b] Review: G. Illuminati, L. Mandolini, Acc. Chem. Res. 1981, 14, 95-102.
12. Crystallographic datas (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101681. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CN2 1EZ, UK [Fax: int. code +44(1223)336-033; E-mail: deposit@ccdc.cam.ac.uk].
13. A. Ullmann, G. Zahn, J. Schnaubelt, H.-U. Reißig, Z. Kristallogr., submitted.
14. [8a] B. Frey, S. Hünig, M. Koch, H.-U. Reißig, Synlett 1991, 854-856.
15. [8b] J. Schnaubelt, R. Zschiesche, H.-U. Reißig, H. J. Lindner, J. Richter, Liebigs Ann. Chem. 1993, 61-70.
16. [8c] J. Schnaubelt, H.-U. Reißig, Synlett 1995, 452-454.
17. For synthesis of a variety of benzanellated compounds (cyclophanes): A. Ullmann, M Gruner, H.-U. Reißig, Chem. Eur. J., im press.
18. [10a] J. Breitenbach, J. Boosfeld, F. Vögtle in Comprehensive Supramolecular Chemistry, vol. 2, 1st ed. (Ed.: F. Vögtle), Pergamon, Oxford, New York, Tokyo, 1996, p. 29-67.
19. [10b] Q. Meng, M. Hesse, Top. Curr. Chem. 1992, 161, 107-176.
20. [10c] C. J. Roxburgh. Tetrahedron 1995, 51, 9767-9822.
21. [10d] M. A. Titus, Chem. Rev. 1988, 88, 719-732.
22. B. Hofmann, H.-U. Reißig, Chem. Ber. 1994, 127, 2315-2325.
23. H. Finkelstein, Ber Dtsch. Chem. Ges. 1910, 43, 1528-1532.
24. G. M. Sheldrick, SHELXS86, 1986, Program for the Solution of Crystal Structures from Diffraction Data, Göttingen.
25. G. M. Sheldrick, SHELXL93, 1993, Program for the Refine ment of Crystal Structures, Göttingen.