Palladium-catalyzed reaction of acylzirconocene chloride and stereoselective formation of bicyclo[3.3.0] compounds

Organic Letters

Volumn 4, Issue 23, 2002, Pages 4061-4064

  Hanzawa, Yuji ^a   Yabe, Masaya ^a   Oka, Yusuke ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0041736688     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026770s     Document Type: Article

References (26)

1. Bertelo, C. A.; Schwartz, J. J. Am. Chem. Soc., 1975, 97, 228.
2. (a) Hanzawa, Y.; Kakuuchi, A.; Yabe, M.; Narita, K.; Tabuchi, N.; Taguchi, T. Tetrahedron Lett. 2001, 42, 1737.
3. (b) Hanzawa, Y.; Narita, K.; Taguchi, T. Tetrahedron Lett. 2000, 41, 109.
4. (c) Kakuuchi, A.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 2001, 42, 1547.
5. (d) Hanzawa, Y.; Tabuchi, N.; Saito, K.; Noguchi, S.; Taguchi, T. Angew. Chem., Int. Ed. 1999, 38, 2395.
6. (e) Hanzawa, Y.; Tabuchi, N.; Taguchi, T. Tetrahedron Lett. 1998, 39, 8141.
7. (f) Hanzawa, Y.; Tabuchi, N.; Taguchi, T. Tetrahedron Lett. 1998, 39, 6249.
8. (g) Harada, S.; Taguchi, T.; Tabuchi, N.; Narita, K.; Hanzawa, Y. Angew. Chem., Int. Ed. 1998, 37, 1696.
9. (a) Montgomery, J. Acc. Chem. Res. 2000, 33, 467.
10. (b) Montgomery, J.; Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J. J. Am. Chem. Soc. 2000, 122, 6775.
11. (c) Montgomery, J.; Oblinger, E.; Savchenko, A. V. J. Am. Chem. Soc. 1997, 119, 4911.
12. Ni, Y.; Amarasinghe, K. K. D.; Montgomery, J. Org. Lett. 2002, 4, 1743.
13. o|), 2θ = 54.26°] and 524 parameters. CCDC-186221.
14. Beesley, R. M.; Ingold, C. K.;, Thorpe, J. F. J. Am. Chem. Soc. 1985, 107, 1080.
15. 3
16. 2 by 1 equiv of DIBAL-H has been reported to give a low-valent nickel catalyst. (a) Dayrit, F. M.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4466.
17. (b) Schwartz, J.; Loots, M. J.; Kosugi, H. J. Am. Chem. Soc. 1980, 702, 1333.
18. (c) Dayrit, F. M.; Gladkowski, D. E.; Schwartz, J. J. Am. Chem. Soc. 1980, 102, 4466.
19. Ester instead of a ketone carbonyl in 3 failed to yield the corresponding product. The length of the tethering chain in 3 or 5 affected the reactivity; that is, a shorter or longer tethering chain did not give the cyclization product.
20. The same type of transformations with Ti complex were reported. (a) Urabe, H.; Suzuki, K.; Sato, F. J. Am. Chem. Soc. 1997, 119, 10014.
21. (b) Suzuki, K.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 1996, 118, 8729.
22. Recently, Montgomery et al. reported the formation of metallacycle through the reaction of alkynyl enals with Ni(0). Amarasinghe, K. K.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370.
23. An attempted trapping of the enolate intermediate with TMSCl gave a complex mixture of products, and we could not isolate the TMS-enol ether.
24. 2AlCl showed reasonable efficiency. The effect of organozinc has been discussed in the Ni-catalyzed reactions. See ref 3.
25. (a) Schore N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Raquette, L. A., Eds; Pergamon: Oxford, UK, 1991; Vol. 5, p 1037.
26. (b) Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds; Pergamon: Oxford, UK, 1991; Vol 5, p 1163 and the references therein.