Lewis acid promoted highly diastereoselective desymmetric intramolecular cyclization of allylstannane with a diketone

Tetrahedron Letters

Volumn 39, Issue 5-6, 1998, Pages 471-474

  Shimada, Takashi ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOTIN COMPOUND;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032576809     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10579-2     Document Type: Article

References (18)

1. 1. For reviews see: (a) Roush, W. R. In Comprehensive Organic Synthesis, Vol. 2, Trost, ed., Pergamon Press: Oxford, 1991, 1.
2. (b) Fleming, I. ibid. 563.
3. (c) Marshall, J. A. Chemtracts, 1992, 5, 75.
4. (d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
5. (e) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395.
6. 2. (a) Yamamoto, Y.; Komatsu, T,; Maruyama, K. J. Chem. Soc., Chem. Commun. 1983, 191.
7. (b) Krämer, T.; Schwark, J. R.; Hoppe, D. Tetrahedron Lett. 1989, 30, 7037.
8. (c) Takuwa, A.; Nishigaichi, Y.; Yamashita, K.; Iwamoto, H. Chem. Lett 1990, 1761.
9. (d) Zhou, J. Y.; Chen, Z. G.; Wu, S. H. J. Chem. Soc., Chem. Commun. 1994, 2783.
10. (e) Denmark, S. E.; Hosoi, S. J. Org. Chem. 1994, 59, 5133.
11. (f) Keck, G. E.; Dougnerty, S. M.; Savin, K. A. J. Am. Chem. Soc. 1995, 117, 6210.
12. (g) Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36, 2721.
13. (h) Yasuda, M.; Sugawa, Y.; Yamamoto, A.; Shibata, L.; Baba, A. Tetrahedron Lett. 1996, 37, 5951.
14. (i) Kadota, I.; Kawada, M.; Saya, S.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2109, and references cited therein.
15. 3. Intramolecular cyclization of allylsilane with diketones: Schinzer, D.; Panke, G. J. Org. Chem. 1996, 61, 4496.
16. 4. Trost, B. M.; Hemdon, J. W. J. Am. Chem. Soc. 1984, 106, 6835.
17. 2 (196.1463), found 196.1460.
18. 6. Destannylated diketone 10 was obtained as a by-product. (equation presented)