Diquinane synthesis based on anionic [1,3] sigmatropic rearrangements of an oxy-cope system incorporated in the bicyclo[3.2.1]oct-6-ene framework

Chemistry Letters

Volumn , Issue 12, 1996, Pages 1035-1036

  Seki, Katsura ^a   Kiyokawa, Wakako ^a   Hashimoto, Hiroki ^a   Uyehara, Tadao ^a   Ueno, Masako ^b   Sato, Toshio ^b  

^a UTSUNOMIYA UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 21444458534     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.1035     Document Type: Article

References (16)

1. For reviews, see: a) L. A. Paquette, Synlett, 1990, 67.
2. b) L. A. Paquette, Angew. Chem., Int. Ed. Engl., 29, 609 (1990).
3. For a review, see: S. R. Wilson, Org. Reaction, 43, 93 (1993).
4. More recent work: a) L. A. Paquette and R. C. Thompson, J. Org. Chem., 58, 4952 (1993).
5. b) L. A. Paquette, S. K. Huber, and R. C. Thompson, J. Org. Chem., 58, 6874 (1993).
6. c) R. Guevel and L. A. Paquette, J. Am. Chem. Soc., 116, 1776 (1994).
7. d) J. Doyon, W. He, and L. A. Paquette, J. Org. Chem., 59, 2033 (1994).
8. e) J.-F. Devaux, I. Hanna, J.-Y. Lallemand, and T. Prange, J. Org. Chem., 58, 2349 (1993).
9. f) K. Mori and Y. Matsushima, Synthesis, 1995, 845.
10. T. Uychara, T. Inayama, M. Ueno, and T. Sato, Chem. Lett., 1996, 389.
11. T. Uychara, T. Inayama, T. Furuta, T. Kato, Y. Yamamoto, M. Ueno, and T. Sato, Bull. Chem. Soc., Jpn., 69, 1727 (1996), and references cited therein.
12. 1H NMR studies including NOE experiments.
13. 3 powder in THF, see: a) T. Imamoto, N. Takiyama, K. Nakamura, T. Hatajima, and Y. Kamiya, J. Am. Chem. Soc., 111, 4392 (1989).
14. b) N. Greeves and L. Lyford, Tetrahedron Lett., 33, 4759 (1992).
15. 3, only the exo alcohol 3c was obtained in 98% yield.
16. An example for the substituent effect in the migrating group of an anionic [1,3] sigmatropic rearrangement, see: T. Uyehara, K. Ohmori, Y. Kabasawa, and T. Kato, Chem. Lett., 1984, 1879.