Organoaluminum-Promoted Cyclization of Olefinic Epoxides. a New and Stereoselective Approach to Cyclohexane Frameworks

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 3, 1997, Pages 707-711

  Murase, Noriaki ^a   Maruoka, Keiji ^b   Ooi, Takashi ^b   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001540610     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.707     Document Type: Article

References (24)

1. Reviews of ring-forming reactions and annulations: a) H. O. House, "Modern Synthetic Reactions," 2nd ed, Benjamin, Menlo Park (1972); b) P. T. Lansbury, Chem. Res., 5, 311 (1972); c) B. P. Mundy, J. Chem. Educ., 50, 110 (1973); d) M. E. Jung, Tetrahedron, 32, 3 (1976); e) R. E. Gawley, Synthesis, 1976, 777; f) B. Giese, Angew. Chem., Int. Ed. Engl., 28, 969 (1989); g) B. M. Trost, Angew. Chem., Int. Ed. Engl., 28, 1173 (1989); h) L. A. Paquette, Angew. Chem., Int. Ed. Engl., 29, 609 (1990).
2. Reviews of ring-forming reactions and annulations: a) H. O. House, "Modern Synthetic Reactions," 2nd ed, Benjamin, Menlo Park (1972); b) P. T. Lansbury, Chem. Res., 5, 311 (1972); c) B. P. Mundy, J. Chem. Educ., 50, 110 (1973); d) M. E. Jung, Tetrahedron, 32, 3 (1976); e) R. E. Gawley, Synthesis, 1976, 777; f) B. Giese, Angew. Chem., Int. Ed. Engl., 28, 969 (1989); g) B. M. Trost, Angew. Chem., Int. Ed. Engl., 28, 1173 (1989); h) L. A. Paquette, Angew. Chem., Int. Ed. Engl., 29, 609 (1990).
3. Reviews of ring-forming reactions and annulations: a) H. O. House, "Modern Synthetic Reactions," 2nd ed, Benjamin, Menlo Park (1972); b) P. T. Lansbury, Chem. Res., 5, 311 (1972); c) B. P. Mundy, J. Chem. Educ., 50, 110 (1973); d) M. E. Jung, Tetrahedron, 32, 3 (1976); e) R. E. Gawley, Synthesis, 1976, 777; f) B. Giese, Angew. Chem., Int. Ed. Engl., 28, 969 (1989); g) B. M. Trost, Angew. Chem., Int. Ed. Engl., 28, 1173 (1989); h) L. A. Paquette, Angew. Chem., Int. Ed. Engl., 29, 609 (1990).
4. Reviews of ring-forming reactions and annulations: a) H. O. House, "Modern Synthetic Reactions," 2nd ed, Benjamin, Menlo Park (1972); b) P. T. Lansbury, Chem. Res., 5, 311 (1972); c) B. P. Mundy, J. Chem. Educ., 50, 110 (1973); d) M. E. Jung, Tetrahedron, 32, 3 (1976); e) R. E. Gawley, Synthesis, 1976, 777; f) B. Giese, Angew. Chem., Int. Ed. Engl., 28, 969 (1989); g) B. M. Trost, Angew. Chem., Int. Ed. Engl., 28, 1173 (1989); h) L. A. Paquette, Angew. Chem., Int. Ed. Engl., 29, 609 (1990).
5. Reviews of ring-forming reactions and annulations: a) H. O. House, "Modern Synthetic Reactions," 2nd ed, Benjamin, Menlo Park (1972); b) P. T. Lansbury, Chem. Res., 5, 311 (1972); c) B. P. Mundy, J. Chem. Educ., 50, 110 (1973); d) M. E. Jung, Tetrahedron, 32, 3 (1976); e) R. E. Gawley, Synthesis, 1976, 777; f) B. Giese, Angew. Chem., Int. Ed. Engl., 28, 969 (1989); g) B. M. Trost, Angew. Chem., Int. Ed. Engl., 28, 1173 (1989); h) L. A. Paquette, Angew. Chem., Int. Ed. Engl., 29, 609 (1990).
6. Reviews of ring-forming reactions and annulations: a) H. O. House, "Modern Synthetic Reactions," 2nd ed, Benjamin, Menlo Park (1972); b) P. T. Lansbury, Chem. Res., 5, 311 (1972); c) B. P. Mundy, J. Chem. Educ., 50, 110 (1973); d) M. E. Jung, Tetrahedron, 32, 3 (1976); e) R. E. Gawley, Synthesis, 1976, 777; f) B. Giese, Angew. Chem., Int. Ed. Engl., 28, 969 (1989); g) B. M. Trost, Angew. Chem., Int. Ed. Engl., 28, 1173 (1989); h) L. A. Paquette, Angew. Chem., Int. Ed. Engl., 29, 609 (1990).
7. Reviews of ring-forming reactions and annulations: a) H. O. House, "Modern Synthetic Reactions," 2nd ed, Benjamin, Menlo Park (1972); b) P. T. Lansbury, Chem. Res., 5, 311 (1972); c) B. P. Mundy, J. Chem. Educ., 50, 110 (1973); d) M. E. Jung, Tetrahedron, 32, 3 (1976); e) R. E. Gawley, Synthesis, 1976, 777; f) B. Giese, Angew. Chem., Int. Ed. Engl., 28, 969 (1989); g) B. M. Trost, Angew. Chem., Int. Ed. Engl., 28, 1173 (1989); h) L. A. Paquette, Angew. Chem., Int. Ed. Engl., 29, 609 (1990).
8. Reviews of ring-forming reactions and annulations: a) H. O. House, "Modern Synthetic Reactions," 2nd ed, Benjamin, Menlo Park (1972); b) P. T. Lansbury, Chem. Res., 5, 311 (1972); c) B. P. Mundy, J. Chem. Educ., 50, 110 (1973); d) M. E. Jung, Tetrahedron, 32, 3 (1976); e) R. E. Gawley, Synthesis, 1976, 777; f) B. Giese, Angew. Chem., Int. Ed. Engl., 28, 969 (1989); g) B. M. Trost, Angew. Chem., Int. Ed. Engl., 28, 1173 (1989); h) L. A. Paquette, Angew. Chem., Int. Ed. Engl., 29, 609 (1990).
9. a) S. F. Martin and S. R. Desai, J. Org. Chem., 42, 1664 (1977);
10. b) S. F. Martin and S. R. Desai, J. Org. Chem., 43, 4673 (1978).
11. R. J. Pariza and P. L. Fuchs, J. Org. Chem., 48, 2304 (1983).
12. P. Magnus, Nouv. J. Chim., 2, 555 (1978).
13. C. M. Hettrick and W. J. Scott, J. Am. Chem. Soc., 113, 4903 (1991).
14. K. Maruoka, N. Murase, T. Ooi, and H. Yamamoto, Synlett, 1991, 857.
15. K. M. Sadhu and D. S. Matteson, Tetrahedron Lett., 27, 795 (1986).
16. Intramolecular ene reaction with MABR: a) K. Maruoka, T. Ooi, and H. Yamamoto, J. Am. Chem. Soc., 111, 6431 (1989); b) K. Maruoka, S. Saito, T. Ooi, and H. Yamamoto, Tetrahedron Lett., 30, 5607 (1989); c) T. Ooi, K. Maruoka, and H. Yamamoto, Tetrahedron, 50, 6505 (1994).
17. Intramolecular ene reaction with MABR: a) K. Maruoka, T. Ooi, and H. Yamamoto, J. Am. Chem. Soc., 111, 6431 (1989); b) K. Maruoka, S. Saito, T. Ooi, and H. Yamamoto, Tetrahedron Lett., 30, 5607 (1989); c) T. Ooi, K. Maruoka, and H. Yamamoto, Tetrahedron, 50, 6505 (1994).
18. Intramolecular ene reaction with MABR: a) K. Maruoka, T. Ooi, and H. Yamamoto, J. Am. Chem. Soc., 111, 6431 (1989); b) K. Maruoka, S. Saito, T. Ooi, and H. Yamamoto, Tetrahedron Lett., 30, 5607 (1989); c) T. Ooi, K. Maruoka, and H. Yamamoto, Tetrahedron, 50, 6505 (1994).
19. For other synthetic applications of MABR, see: a) K. Maruoka, K. Nonoshita, H. Banno, and H. Yamamoto, J. Am. Chem. Soc., 110, 7922 (1988); b) K. Maruoka, H. Banno, K. Nonoshita, and H. Yamamoto, Tetrahedron Lett., 30, 1265 (1989); c) K. Nonoshita, H. Banno, K. Maruoka, and H. Yamamoto, J. Am. Chem. Soc., 112, 316 (1990); d) K. Maruoka, J. Sato, H. Banno, and H. Yamamoto, Tetrahedron Lett., 31, 377 (1990).
20. For other synthetic applications of MABR, see: a) K. Maruoka, K. Nonoshita, H. Banno, and H. Yamamoto, J. Am. Chem. Soc., 110, 7922 (1988); b) K. Maruoka, H. Banno, K. Nonoshita, and H. Yamamoto, Tetrahedron Lett., 30, 1265 (1989); c) K. Nonoshita, H. Banno, K. Maruoka, and H. Yamamoto, J. Am. Chem. Soc., 112, 316 (1990); d) K. Maruoka, J. Sato, H. Banno, and H. Yamamoto, Tetrahedron Lett., 31, 377 (1990).
21. For other synthetic applications of MABR, see: a) K. Maruoka, K. Nonoshita, H. Banno, and H. Yamamoto, J. Am. Chem. Soc., 110, 7922 (1988); b) K. Maruoka, H. Banno, K. Nonoshita, and H. Yamamoto, Tetrahedron Lett., 30, 1265 (1989); c) K. Nonoshita, H. Banno, K. Maruoka, and H. Yamamoto, J. Am. Chem. Soc., 112, 316 (1990); d) K. Maruoka, J. Sato, H. Banno, and H. Yamamoto, Tetrahedron Lett., 31, 377 (1990).
22. For other synthetic applications of MABR, see: a) K. Maruoka, K. Nonoshita, H. Banno, and H. Yamamoto, J. Am. Chem. Soc., 110, 7922 (1988); b) K. Maruoka, H. Banno, K. Nonoshita, and H. Yamamoto, Tetrahedron Lett., 30, 1265 (1989); c) K. Nonoshita, H. Banno, K. Maruoka, and H. Yamamoto, J. Am. Chem. Soc., 112, 316 (1990); d) K. Maruoka, J. Sato, H. Banno, and H. Yamamoto, Tetrahedron Lett., 31, 377 (1990).
23. The isomeric purity of 7 is ca. 96% by capillary GLC analysis.
24. T. K. Devon and A. I. Scott, "Handbook of Naturally Occurring Compounds - Volume II, Terpenes," Academic Press, New York (1972).