Novel synthesis of heterocycles using nickel(0)-catalyzed [2+2+2] cocyclization: Catalytic asymmetric synthesis of isoindoline and isoquinoline derivatives

Heterocycles

Volumn 44, Issue 1, 1997, Pages 443-457

  Sato, Yoshihiro ^a   Nishimata, Toyoki ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006890108     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-96-s43     Document Type: Article

References (32)

1. (a) K. P. C. Vollhardt, Angew. Chem., Int. Ed. Engl., 1984, 23, 539 and references cited therein,
2. (b) K. P. C. Vollhardt, Acc. Chem. Res., 1977, 10, 1.
3. (a) R. Grigg, R. Scott, and P. Stevenson, J. Chem. Soc., Perkin Trans. 1, 1988, 1357.
4. (b) R. Grigg, R. Scott, and P. Stevenson, Tetrahedron Lett., 1982, 23, 2691.
5. (c) S. J. Neeson and P. J. Stevenson, Tetrahedron, 1989, 45, 6239.
6. (d) S. J. Neeson and P. J. Stevenson, Tetrahedron Lett., 1988, 29, 813.
7. (a) P. Bhatarah and E. H. Smith, J. Chem. Soc., Perkin Trans. 1, 1992, 2163.
8. (b) P. Bhatarah and E. H. Smith, J. Chem. Soc., Chem. Comm., 1991, 277.
9. (c) P. Bhatarah and E. H. Smith, J. Chem. Soc., Perkin Trans, 1, 1990, 2603.
10. It was reported that the reaction of a hepta-1,6-diyne and a monosubstituted alkyne using a stoichiometric amount of nickel(0) complex afforded indane derivatives in good to moderate yields. However, it was also reported that the reaction using a catalytic amount of nickel(0) complex (20 mol %) went to 40-50% completion. See ref. 3 (c).
11. Preliminary Communication: Y. Sato, T. Nishimata, and M. Mori, J. Org. Chem., 1994, 59, 6133.
12. For some elegant examples of the catalytic asymmetric construction of the chiral carbon centers at the benzylic position, see: (a) R. Noyori, M. Ohta, Y. Hsiao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 1986, 108, 7117.
13. (b) M. Kitamura, Y. Hsiao, M. Ohta, M. Tsukamoto, T. Ohta, H. Takaya, and R. Noyori, J. Org. Chem., 1994, 59, 297.
14. (c) T. Takemoto, M. Sodeoka, H. Sasai, and M. Shibasaki, J. Am. Chem. Soc., 1993, 115, 8477.
15. For examples of asymmetric synthesis of tetrahydroisoquinolines, see: (a) A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 1987, 43, 5095.
16. (b) M. J. Munchhof and A. I. Meyers, J. Org. Chem., 1995, 60, 7086.
17. (c) A. C. Carbonnelle, V. Gott, and G. Roussi, Heterocycles, 1993, 36, 1763.
18. (d) M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 1990, 46, 5909.
19. (e) R. P. Polniaszek and L. W. Dillard, Tetrahedron Lett., 1990, 31, 797.
20. (f) I. M. P. Huber and D. Seebach, Helv. Chim. Acta, 1987, 70, 1944.
21. M. Wada, Y. Sakurai, and K. Akiba, Tetrahedron Lett., 1984, 25, 1083.
22. (a) H. B. Kagan, 'Asymmetric Synthesis', Vol. 5, ed. by J. D. Morrison, Academic Press, Inc., 1985, p. 1 and references cited therein,
23. (b) R. H. Grubbs and R. A. DeVries, Tetrahedron Lett., 1977, 1879;
24. B. M. Trost and D. J. Murphy, Organometallics, 1985, 4, 1143.
25. T. Hayashi and M. Kumada, 'Asymmetric Synthesis', Vol. 5, ed.by J. D. Morrison, Academic Press, Inc., 1985, p. 147.
26. Y. Uozumi and T. Hayashi, J. Am. Chem. Soc., 1991, 113, 9887;
27. Y. Uozumi, A. Tanahashi, S.-Y. Lee, and T. Hayashi, J. Org. Chem., 1993, 58, 1945.
28. (a) Z. Horii, M. Ikeda, Y. Yamawaki, Y. Tamaru, S. Saito, and K. Kodera, Tetrahedron, 1963, 19, 2101.
29. (b) J. C. Craig, R. P. K. Chan, and S. K. Roy, Tetrahedron, 1967, 23, 3573. Also see ref. 7 (a).
30. K. Ito and H. Tanaka, Chem. Pharm. Bull., 1977, 25, 1732.
31. G. P. Chiusoli, M. Costa, and S. Reverbeli, Synthesis, 1989, 262.
32. J. Bornstein and J. E. Shields, Org. Synth., Coll. Vol., 5, 1973, p. 1064.