BF3·Et2O-Mediated Intramolecular Allylstannane-Ketone Cyclizations: Formation of Bicyclo[4.1.0]hept-4-en-1-ols from 5-(Tributylstannyl)-3-cycloheptenones

Synlett

Volumn 1996, Issue 8, 1996, Pages 753-754

  Takeda, Kei ^a   Nakajima, Akemi ^a   Yoshii, Eiichi ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000879752     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5506     Document Type: Article

References (12)

1. Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 177, 6400-6401.
2. 2SiSn 600.3385, Found 600.3428.
3. The acylsilanes (E,Z)-1 were prepared from 1-(tert-butyldimethylsilyl)-1-(1-ethoxyethoxy)-1,2-propadiene according to the procedure of Reich and co-workers for the corresponding β-trimethylsilyl derivatives. Reich, H. J.; Kelly, M. J.; Olson, R. E.; Holtan, R. C. Tetrahedron 1983, 39, 949-960.
4. For air oxidation of 1,2-cyclopropanediol derivatives to 1,3-diketones, see: Priddy, D. B.; Reusch, W. Tetrahedron Lett. 1970, 2637-2640.
5. (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293.
6. (b) Nishiguchi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395-7426.
7. 2Si 310.2328, found 310.2338. The stereochemistry at C-4 was assigned on the basis of observed correlation between the hydrogens at C-4 and C-7 in NOESY experiments.
8. (a) Denmark, S. E.; Weber, E. J. J. Am. Chem. Soc. 1984, 106, 7970-7971.
9. (b) Young, D.; Kitching, W.; Wickham, G. Tetrahedron Lett. 1983, 5789-5792, 5793-5796.
10. (c) Young, D.; Kitching, W. J. Org. Chem. 1983, 48, 612-614.
11. See also: (d) Marshall, J. A.; Hinkel, K. W. J. Org. Chem. 1996, 61, 105-108 and references cited therein.
12. Kadota, I.; Matsukawa, Y.; Yamamoto, Y. J. Chem. Soc. Chem. Commun. 1993, 1638-1641.