Synthesis of Five-, Six-, and Seven-Membered Heterocycles by Intramolecular Ring Opening Reactions of 3-Oxetanol Derivatives

Journal of Organic Chemistry

Volumn 63, Issue 6, 1998, Pages 1910-1918

  Bach, Thorsten ^a   Kather, Kristian ^b   Krämer, Oliver ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001382823     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971866z     Document Type: Article

References (40)

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5. Reviews: (a) Kropf, H.; Thiem, J.; Nimz, H. In Methoden der Organischen Chemie (Houben-Weyl), 4th ed.; Kropf, H., Ed.; Thieme: Stuttgart, 1979; Vol. VI/1a, p 338. (b) Lewars, E. G. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Ed.; Pergamon Press: Oxford 1984; Vol. 7, p 96.
6. General reviews on oxetane ring opening: (a) Searles, S. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Ed.; Wiley-Interscience: New York, 1964; Vol. 19-2, p 983. (b) Searles, S. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Ed.; Pergamon Press: Oxford, 1984; Vol. 7, p 363.
7. General reviews on oxetane ring opening: (a) Searles, S. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Ed.; Wiley-Interscience: New York, 1964; Vol. 19-2, p 983. (b) Searles, S. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Ed.; Pergamon Press: Oxford, 1984; Vol. 7, p 363.
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24. Intermolecular ring opening by sulfur nucleophiles: (a) Searles, S. J. Am. Chem. Soc. 1951, 73, 4515. (b) Whistler, R. L.; Luttenegger, T. J.; Powell, R. M. J. Org. Chem. 1968, 33, 396. (c) Godziela, G.; Tonker, T.; DuBois, M. R. Organometallics 1989, 8, 2220. (d) Xianming, H.; Kellogg, R. M. Tetrahedron: Asymmetry 1995, 6, 1399.
25. Intermolecular ring opening by sulfur nucleophiles: (a) Searles, S. J. Am. Chem. Soc. 1951, 73, 4515. (b) Whistler, R. L.; Luttenegger, T. J.; Powell, R. M. J. Org. Chem. 1968, 33, 396. (c) Godziela, G.; Tonker, T.; DuBois, M. R. Organometallics 1989, 8, 2220. (d) Xianming, H.; Kellogg, R. M. Tetrahedron: Asymmetry 1995, 6, 1399.
26. Intermolecular ring opening by nitrogen nucleophiles: (a) Searles, S.; Gregory, V. P. J. Am. Chem. Soc. 1954, 76, 2789. (b) Mullis, J. C.; Weber, W. P. J. Org. Chem. 1982, 47, 2873. (c) Gassman, P. G.; Haberman, L. M. Tetrahedron Lett. 1985, 26, 4971. (d) Chini, M.; Crotti, P.; Favero, L.; Macchia, F. Tetrahedron Lett. 1994, 35, 761. (e) Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 7089. (f) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597.
27. Intermolecular ring opening by nitrogen nucleophiles: (a) Searles, S.; Gregory, V. P. J. Am. Chem. Soc. 1954, 76, 2789. (b) Mullis, J. C.; Weber, W. P. J. Org. Chem. 1982, 47, 2873. (c) Gassman, P. G.; Haberman, L. M. Tetrahedron Lett. 1985, 26, 4971. (d) Chini, M.; Crotti, P.; Favero, L.; Macchia, F. Tetrahedron Lett. 1994, 35, 761. (e) Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 7089. (f) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597.
28. Intermolecular ring opening by nitrogen nucleophiles: (a) Searles, S.; Gregory, V. P. J. Am. Chem. Soc. 1954, 76, 2789. (b) Mullis, J. C.; Weber, W. P. J. Org. Chem. 1982, 47, 2873. (c) Gassman, P. G.; Haberman, L. M. Tetrahedron Lett. 1985, 26, 4971. (d) Chini, M.; Crotti, P.; Favero, L.; Macchia, F. Tetrahedron Lett. 1994, 35, 761. (e) Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 7089. (f) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597.
29. Intermolecular ring opening by nitrogen nucleophiles: (a) Searles, S.; Gregory, V. P. J. Am. Chem. Soc. 1954, 76, 2789. (b) Mullis, J. C.; Weber, W. P. J. Org. Chem. 1982, 47, 2873. (c) Gassman, P. G.; Haberman, L. M. Tetrahedron Lett. 1985, 26, 4971. (d) Chini, M.; Crotti, P.; Favero, L.; Macchia, F. Tetrahedron Lett. 1994, 35, 761. (e) Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 7089. (f) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597.
30. Intermolecular ring opening by nitrogen nucleophiles: (a) Searles, S.; Gregory, V. P. J. Am. Chem. Soc. 1954, 76, 2789. (b) Mullis, J. C.; Weber, W. P. J. Org. Chem. 1982, 47, 2873. (c) Gassman, P. G.; Haberman, L. M. Tetrahedron Lett. 1985, 26, 4971. (d) Chini, M.; Crotti, P.; Favero, L.; Macchia, F. Tetrahedron Lett. 1994, 35, 761. (e) Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 7089. (f) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597.
31. Intermolecular ring opening by nitrogen nucleophiles: (a) Searles, S.; Gregory, V. P. J. Am. Chem. Soc. 1954, 76, 2789. (b) Mullis, J. C.; Weber, W. P. J. Org. Chem. 1982, 47, 2873. (c) Gassman, P. G.; Haberman, L. M. Tetrahedron Lett. 1985, 26, 4971. (d) Chini, M.; Crotti, P.; Favero, L.; Macchia, F. Tetrahedron Lett. 1994, 35, 761. (e) Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 7089. (f) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597.
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37. For related epoxide ring opening reactions, see: (a) Minami, N.; Ko, S. S.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1109. (b) Corey, E. J.; Hopkins, P. B.; Munroe, J. E.; Marfat, A.; Hashimoto, S.-i. J. Am. Chem. Soc. 1980, 102, 7986. (c) Roush, W. R.; Brown, R. J.; DiMare, M. J. Org. Chem. 1983, 48, 5083.
38. For related epoxide ring opening reactions, see: (a) Minami, N.; Ko, S. S.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1109. (b) Corey, E. J.; Hopkins, P. B.; Munroe, J. E.; Marfat, A.; Hashimoto, S.-i. J. Am. Chem. Soc. 1980, 102, 7986. (c) Roush, W. R.; Brown, R. J.; DiMare, M. J. Org. Chem. 1983, 48, 5083.
39. For related epoxide ring opening reactions, see: (a) Minami, N.; Ko, S. S.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1109. (b) Corey, E. J.; Hopkins, P. B.; Munroe, J. E.; Marfat, A.; Hashimoto, S.-i. J. Am. Chem. Soc. 1980, 102, 7986. (c) Roush, W. R.; Brown, R. J.; DiMare, M. J. Org. Chem. 1983, 48, 5083.
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