Titanium- And Lewis acid-mediated cyclopropanation of imides

Organic Letters

Volumn 9, Issue 4, 2007, Pages 659-662

  Bertus, Philippe ^a   Szymoniak, Jan ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33847793194     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062938o     Document Type: Article

References (35)

1. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevsky, D. A.; Pritytskaja, T. S. Zh. Org. Khim. 1989, 25, 2244-2245;
2. J. Org. Chem. USSR 1989, 25, 2027-2028.
3. Reviews: (a) Kulinkovich, O. G. Ear. J. Org. Chem. 2004, 4517-4529.
4. (b) de Meijere, A.; Kozhushkov, S. I.; Savchenko, A. I. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 390-434.
5. (c) de Meijere, A.; Kulinkovich, O. G. Chem. Rev. 2000, 100, 2789-2834.
6. Review: de Meijere, A.; Kozhushkov, S. I.; Savchenko, A. I. J. Organomet. Chem. 2004, 689, 2033-2055.
7. Lee, J.; Kim, Y. G.; Bae, J. G.; Cha, J. K. J. Org. Chem. 1996, 61, 4878-4879.
8. (a) Lee, J.; Ha, J. D.; Cha, J. K. J. Am. Chem. Soc. 1997, 119, 8127-8128.
9. (b) Lee, K.; Kim, S.-E.; Cha, J. K. J. Org. Chem. 1998, 63, 9135-9138.
10. (c) Sung, M. J.; Lee, C.-W.; Cha, J. K. Synlett 1999, 561-562.
11. (d) Kim, S.-H.; Park, Y.; Choo, H.; Cha, J. K. Tetrahedron Lett. 2002, 43, 6657-6660.
12. (e) Santra, S. Masalov, N.; Epstein, O.; Cha, J. K. Org. Lett. 2005, 7, 5901-5904.
13. Similarly to imides, N-acylpyrroles did not afford cyclopropane derivatives under Kulinkovich conditions; see: Epstein, O. L.; Seo, J. M.; Masalov, N.; Cha, J. K. Org. Lett. 2005, 7, 2105-2108.
14. (a) Kim, S.-H.; Kim, S.-I.; Lai, S.; Cha, J. K. J. Org. Chem. 1999, 64, 6771-6775.
15. (b) Kim, S.-H.; Cha, J. K. Synthesis 2000, 2113-2116.
16. (c) Ollero, L.; Mentink, G.; Rutjes, F. P. J. T.; Speckamp, W. N.; Hiemstra, H. Org. Lett. 1999, 1, 1331-1334.
17. (a) Bertus, P.; Szymoniak, J. Chem. Commun. 2001, 1792-1793.
18. (b) Bertus, P.; Szymoniak, J. J. Org. Chem. 2002, 67, 3965-3968.
19. (c) Bertus, P.; Szymoniak, J. Synlett 2003, 265-267.
20. (d) Laroche, C.; Bertus, P.; Szymoniak, J. Tetrahedron Lett. 2003, 44, 2485-2487.
21. (e) Bertus, P.; Szymoniak, J. J. Org. Chem. 2003, 68, 7133-7136.
22. (f) Laroche, C.; Harakat, D.; Bertus, P.; Szymoniak, J. Org. Biomol. Chem. 2005, 3, 3482-3487.
23. (g) Laroche, C.; Behr, J.-B.; Szymoniak, J.; Bertus, P.; Plantier-Royon, R. Eur. J. Org. Chem. 2005, 5084-5088.
24. See also: (h) Gensini, M.; Kozhushkov, S. I.; Yufit, D. S.; Howard, J. A. K.; Es-Sayed, M.; de Meijere, A. Eur. J. Org. Chem. 2002, 2499-2507.
25. Closely related to imides, acyloxazolidinones afforded cyclopropanols under Kulinkovich conditions; see: Mizojiri, R.; Urabe, H.; Sato, F. J. Org. Chem. 2000, 65, 6217-6222.
26. (a) According to the referee's remark, 4 could also arise from the Lewis acid coordination on the alkoxy ligands. (b) Another site of coordination is the nitrogen atom. The expected final product would be the same as that in path a, i. e., the cyclopropanol 3.
27. 3 and MeLi; see: Reetz, M. T.; Westermann, J.; Steinbach, R.; Wenderoth, B.; Peter, R.; Ostarek, R.; Maus, S. Chem. Ber. 1985, 118, 1421-1440.
28. 4: Chaplinski, V.: Winsel, H.; Kordes, M.; de Meijere, A. Synlett 1997, 111-114.
29. Acyclic imides are known to be much more reactive toward nucleophiles than the cyclic ones. See, for example: (a) Murakami, Y.; Kondo, K.; Miki, K.; Akiyama, Y.; Watanabe, T.; Yokoyama, Y. Tetrahedron Lett. 1997, 38, 3751-3754.
30. (b) Sykes, N. O.; Macdonald, S. J. F.; Page, M. I. J. Med. Chem. 2002, 45, 2850-2856.
31. The relative stereochemistry of compounds 8a-e has not been established.
32. Only two methods for preparing the tricyclic core of 8a were reported in the literature, whereas the other polycyclic frameworks of 8b-e are unknown to date: (a) Hanessian, S.; Buckle, R.; Bayrakdarian, M. J. Org. Chem. 2002, 67, 3387-3397.
33. (b) Beak, P.; Wu, S.; Yum, E. K.; Jun, Y. M. J. Org. Chem. 1994, 59, 276-277.
34. (a) Michael, J. P. Nat. Prod. Rep. 2005, 22, 603-626.
35. (b) Liddell, J. R. Nat. Prod. Rep. 2002, 19, 773-781 and references therein.