Regiocontrol of radical cyclization by Lewis acids. Efficient synthesis of optically active functionalized cyclopentanes and cyclohexanes

Organic Letters

Volumn 3, Issue 1, 2001, Pages 67-69

  Kim, Kwangho ^a   Okamoto, Sentaro ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

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ARTICLE;

EID: 0002444254     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0067890     Document Type: Article

References (29)

1. For radical-mediated substituted cycloalkane construction: Zhu, Q.; Qiao, L.-X.; Wu, Y.; Wu, Y.-L. J. Org. Chem. 1999, 64, 2428 and references therein.
2. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
3. 3Al (Ooi, T.; Kagoshima, N.; Ichikawa, H.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 3228) did not take place.
4. 3Al (Ooi, T.; Kagoshima, N.; Ichikawa, H.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 3228) did not take place.
5. 3Al (Ooi, T.; Kagoshima, N.; Ichikawa, H.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 3228) did not take place.
6. Reviews for synthetic reactions mediated by the titanium(II) reagenf Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511. Sato, F.; Urabe, H.; Okamoto, S. Synlett 2000, 753, Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100. 2835.
7. Reviews for synthetic reactions mediated by the titanium(II) reagenf Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511. Sato, F.; Urabe, H.; Okamoto, S. Synlett 2000, 753, Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100. 2835.
8. Reviews for synthetic reactions mediated by the titanium(II) reagenf Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511. Sato, F.; Urabe, H.; Okamoto, S. Synlett 2000, 753, Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100. 2835.
9. For a Ti(II)-mediated synthesis of α-alkylidenelactones from alkynyl carbonates: Kasatkin, A.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1995, 36, 6075. Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208. Mincheva, Z. P.; Gao, Y.; Sato, F. Tetrahedron Lett. 1998, 39, 7947.
10. For a Ti(II)-mediated synthesis of α-alkylidenelactones from alkynyl carbonates: Kasatkin, A.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1995, 36, 6075. Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208. Mincheva, Z. P.; Gao, Y.; Sato, F. Tetrahedron Lett. 1998, 39, 7947.
11. For a Ti(II)-mediated synthesis of α-alkylidenelactones from alkynyl carbonates: Kasatkin, A.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1995, 36, 6075. Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208. Mincheva, Z. P.; Gao, Y.; Sato, F. Tetrahedron Lett. 1998, 39, 7947.
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14. Review: Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753. Selective 6-endo-cyclization of 5-carbomethoxy-5-hexenyl radicals via a conjugate addition pathway was reported: Delia, E. W.; Kostakis, C.; Smith, P. A. Org. Lett. 1999, 1, 363. See also: Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063. Tararov, V. I.; Kuznetzov, N. Y.; Bakhmutov, V. I.; Ikonnikov, N. S.; Bubnov, Y. N.; Khrustalev, V. N.; Saveleva, T. F.; Belokon, Y. N. J. Chem. Soc., Perkin Trans. 1 1997, 3101.
15. Review: Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753. Selective 6-endo-cyclization of 5-carbomethoxy-5-hexenyl radicals via a conjugate addition pathway was reported: Delia, E. W.; Kostakis, C.; Smith, P. A. Org. Lett. 1999, 1, 363. See also: Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063. Tararov, V. I.; Kuznetzov, N. Y.; Bakhmutov, V. I.; Ikonnikov, N. S.; Bubnov, Y. N.; Khrustalev, V. N.; Saveleva, T. F.; Belokon, Y. N. J. Chem. Soc., Perkin Trans. 1 1997, 3101.
16. Review: Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753. Selective 6-endo-cyclization of 5-carbomethoxy-5-hexenyl radicals via a conjugate addition pathway was reported: Delia, E. W.; Kostakis, C.; Smith, P. A. Org. Lett. 1999, 1, 363. See also: Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063. Tararov, V. I.; Kuznetzov, N. Y.; Bakhmutov, V. I.; Ikonnikov, N. S.; Bubnov, Y. N.; Khrustalev, V. N.; Saveleva, T. F.; Belokon, Y. N. J. Chem. Soc., Perkin Trans. 1 1997, 3101.
17. Review: Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753. Selective 6-endo-cyclization of 5-carbomethoxy-5-hexenyl radicals via a conjugate addition pathway was reported: Delia, E. W.; Kostakis, C.; Smith, P. A. Org. Lett. 1999, 1, 363. See also: Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063. Tararov, V. I.; Kuznetzov, N. Y.; Bakhmutov, V. I.; Ikonnikov, N. S.; Bubnov, Y. N.; Khrustalev, V. N.; Saveleva, T. F.; Belokon, Y. N. J. Chem. Soc., Perkin Trans. 1 1997, 3101.
18. One reviewer suggested that regiospecific production of 5-exo product for the case of 3c and 3d might lie in product radical stability (such as benzyl and α-silyl radicals).
19. Review for use of Lewis acids in radical reactions: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562.
20. Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576. Urabe, H.; Kobayashi, K.; Sato, F. J. Chem. Soc., Chem. Comm. 1995, 1043-1044.
21. Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576. Urabe, H.; Kobayashi, K.; Sato, F. J. Chem. Soc., Chem. Comm. 1995, 1043-1044.
22. Vionnet, J.-P.; Schenk, K.; Renaud, P. Helv. Chim. Acta 1993, 76, 2490. Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 274.
23. Vionnet, J.-P.; Schenk, K.; Renaud, P. Helv. Chim. Acta 1993, 76, 2490. Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 274.
24. In comparison with intermolecular reaction, a change in regioselectivity in intramolecular reaction seems to be more difficult, since it needs to overcome the stereoelectronic effect.
25. The reaction mainly resulted in reduction of the olefin and iodo moieties.
26. Fuji, K. Chem. Rev. 1993, 93, 2037.
27. Although the conversion of 2a was carried out in the presence of 8% of 1a, due to the difficulty of the separation by column chromatography, pure 10, 11 and 12 were obtained after purification by column chromatography.
28. (a) Greene, A. E.; Depres, J. P.; Coelho, F.; Brocksom, T. J. J. Org. Chem. 1985, 50, 3945.
29. (b) Greene, A. E.; Coelho, F.; Depres, J. P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661.