Titanium-mediated alkylative cyclizations of 1,3-diene-tethered esters

Organic Letters

Volumn 3, Issue 17, 2001, Pages 2745-2747

  Quan, Long Guo ^a   Cha, Jin Kun ^a  

^a UNIVERSITY OF ALABAMA   (United States)

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ARTICLE;

EID: 0011843549     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016350n     Document Type: Article

References (36)

1. For general reviews, see: (a) Negishi, E.-i. Acc. Chem. Res. 1987, 20, 65.
2. (b) Negishi, E.-i.; Takahashi, T. Synthesis 1988, 1.
3. (c) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047.
4. (d) Takahashi, T. J. Synth. Org. Jpn. 1993, 51, 1145.
5. (e) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
6. For representative examples, see: (a) Hewlett, D. F.; Whitby, R. J. J. Chem. Soc., Chem. Commun. 1990, 1684.
7. (b) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785.
8. (c) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787.
9. (d) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182.
10. (e) Montgomery, J. Acc. Chem. Res. 2000, 33, 467.
11. See, inter alia: (a) Yasuda, H.; Tatsumi, K.; Nakamura, A. Acc. Chem. Res. 1985, 18, 120.
12. (b) Sato, Y.; Takimoto, M.; Hayashi, K.; Katsuhara, T.; Takagi, K.; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771.
13. (c) Sato, Y.; Takimoto, M.; Mori, M. Tetrahedron Lett. 1996, 37, 887.
14. (d) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521.
15. (e) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033.
16. (f) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397.
17. For recent reviews, see; (a) Kulinkovich, O. G.; de Meijere, A. Chem. Rev. 2000, 100, 2789.
18. (b) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835.
19. (c) Sato, F.; Urabe, H.; Okamoto, S. Synlett 2000, 753.
20. Compare Hudlicky, T.; Sheth, J. P. Tetrahedron Lett. 1979, 2667.
21. 2 (10 mL). and the combined filtrates were concentrated under vacuum. Purification by column chromatography on silica gel afforded 84.3 mg (81%) of 6. When 1.8 equiv of cyclopentylmagnesium chloride (e.g., 0.45 mL of a 2.0 M solution in THF) was employed under otherwise identical conditions, 1 (77 mg, 0.5 mmol) gave 38.5 mg (62%) of 3a and 20.4 mg (21%) of 4a.
22. The stereochemistry of 2-alkenylcyclopentanols and -cyclohexanols can be easily determined by the diagnostic chemical shift of the methine proton, which is more shielded in trans isomers than in cis isomers: Snider, B. B.; Karras, M.; Price, R. T.; Rodini, D. J. J. Org. Chem. 1982, 47, 4538.
23. Compare Lee, J. C.; Sung, M. J.; Cha, J. K. Tetrahedron Lett. 2001, 42, 2059.
24. Chaplinski, V.; Winsel, H.; Kordes, M.; de Meijere, A. Synlett 1997, 111.
25. Compare (a) Kulinkovich, O. G.; Savchenko, A. I.; Sviridov, S. V.; Vasilevski, D. A. Mendeleev Commun. 1993, 230.
26. (b) Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079.
27. (c) Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291.
28. (d) Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198.
29. Williams, C. M.; Chaplinski, V.; Schreiner, P. R.; de Meijere, A. Tetrahedron Lett. 1998, 39, 7695.
30. Similar rearrangements have been reported for zirconocene-diene complexes: (a) Erker, G.; Dorf, U. Angew. Chem., Int. Ed. Engl. 1983, 22. 777.
31. (b) Erker, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 397.
32. (a) Zubaidha, P. K.; Kasatkin, A.; Sato, F. J. Chem. Soc., Chem. Commun. 1996, 197. Compare
33. (b) Yoshida, Y.; Okamoto, S.; Sato, F. J. Org. Chem. 1996, 61, 7826.
34. (a) See footnote 11 of ref 11.
35. (b) Lee, J.; Quan, L. G.; Cha, J. K., unpublished observations.
36. (c) For an alternative approach, see: Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919.