Intramolecular reaction of oxo-substituted allenyl- and propargylstannane with aldehyde

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 3059-3062

  Kadota, Isao ^a   Hatakeyama, Daigo ^a   Seki, Katsura ^a,b   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b UTSUNOMIYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; OXEPANE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029897844     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00469-8     Document Type: Article

References (20)

1. (a) Yamamoto, Y.; Yamada, J.; Kadota, I. Tetrahedron Lett. 1991, 32, 7069-7072.
2. (b) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313-1316.
3. (c) Yamamoto, Y.; Kadota, I. Main Group Met. Chem. 1994, 17, 269-289.
4. Kadota, I.; Park, J.-Y.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777-5780.
5. (a) Suzuki, T.; Sato, O.; Hirama, M.; Yamamoto, Y.; Murata, M.; Yasumoto, T.; Harada, N. Tetrahedron Lett. 1991, 32, 4505-4508.
6. (b) Ravelo, J. L.; Regueiro, A.; Martin, J. D. Tetrahedron Lett. 1992, 33, 3389-3392.
7. (c) Alvarez, E.; Díaz, M. T.; Pérez, R.; Ravelo, J. L.; Regueiro, A.; Vera, J. A.; Zurita, D.; Martín, J. D. J. Org. Chem. 1994, 59, 2848-2870.
8. (d) Kadota, I.; Matsukawa, Y.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1993, 1638-1641.
9. (e) Yamamoto, Y.; Kadota, I. Bull. Soc. Chim. Belg. 1994, 703, 619-629.
10. (f) Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martín, J. D. Chem. Rev. 1995, 95, 1953-1980.
11. (g) Oguri, H.; Hishiyama, S.; Oishi, T.; Hirama, M. Synlett 1995, 1252-1254.
12. For reviews on the chemistry of allenyl and propargyl organometallics, see: (a) Yamamoto, H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, p 81-98.
13. (b) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, p 975-1006.
14. For recent examples of the intermolecular reaction of allenyl-and propargylstannanes with aldehydes; see: (a) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1990, 55, 6246-6250.
15. (b) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1992, 57, 1242-1252.
16. (c) Marshall, J. A.; Perkins, J. J. Org. Chem. 1994, 59, 3509-3511.
17. (d) Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550-5555.
18. (e) Marshall, J. A.; Perkins, J. F.; Wolf, M. A. J. Org. Chem. 1995, 60, 5556-5559.
19. 3 has been reported; see ref 5c and d.
20. Narasaka, K.; Morikawa, A.; Saigo, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 2773-2776.