Titanium-mediated [4 + 1] assembly of 1,3-dienes and nitriles: Formation of 3-cyclopentenyl amines and cyclopentenones

Chemical Communications

Volumn , Issue 24, 2005, Pages 3030-3032

  Laroche, Christophe ^a   Bertus, Philippe ^a   Szymoniak, Jan ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIENE DERIVATIVE; 3 CYCLOPENTENYL DERIVATIVE; ALKADIENE; AMINE; CYCLOPENTENONE; NITRILE; PRASEODYMIUM; TITANIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; METAL BINDING; REACTION ANALYSIS; ROOM TEMPERATURE; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 21844436873     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b503643g     Document Type: Article

References (36)

1. (a) M. Beller and C. Bolm, Transition metals for organic synthesis, Wiley-VCH, Weinheim, 2004;
2. (b) I. Ojima, M. Tzamarioudaki, Z. Li and R. J. Donovan, Chem. Rev., 1996, 96, 635-662;
3. (c) M. Lautens, W. Klute and W. Tam, Chem. Rev., 1996, 96, 49-92.
4. (a) S. E. Gibson, S. E. Lewis and N. Mainolfi, J. Organomet. Chem., 2004, 689, 3873-3890 and references therein;
5. (b) M. E. Welker, Chem. Rev., 1992, 92, 97-112;
6. (c) S. Yamago and E. Nakamura, Org. React., 2002, 61, 1-217;
7. (d) H. L. Stokes, L. Ni, J. A. Belot and M. E. Welker, J. Organomet. Chem., 1995, 487, 95-104.
8. (a) J. Barluenga, S. Lopéz and J. Flórez, Angew. Chem., Int. Ed., 2003, 42, 231-233;
9. (b) S. V. Gagnier and R. C. Larock, J. Am. Chem. Soc., 2003, 125, 4804-4807;
10. (c) E. Negishi, S. Ma, J. Amanfu, C. Copéret, J. A. Miller and J. M. Tour, J. Am. Chem. Soc., 1996, 118, 5919-5931;
11. (d) M. A. Sierra, B. Soderberg, P. A. Lander and L. S. Hegedus, Organometallics, 1993, 12, 3769-3771;
12. (e) M. Franck-Neumann, E. L. Michelotti, R. Simler and J.-M. Vernier, Tetrahedron Lett., 1992, 33, 7361-7364;
13. (f) B. E. Eaton and B. Rollman, J. Am. Chem. Soc., 1992, 114, 6245-6246 and references therein.
14. (a) G. Erker, G. Kehr and R. Fröhlich, Adv. Organomet. Chem., 2004, 51, 109-162;
15. (b) G. Erker, G. Kehr and R. Fröhlich, J. Organomet. Chem., 2004, 689, 4305-4318;
16. (c) A. Nakamura and A. Mashima, J. Organomet. Chem., 2004, 689, 4552-4563.
17. 2-zirconacyclopentenes, leading to both open-chain and cyclic final products, see: E. Negishi and S. Huo, in Titanium and Zirconium in Organic Synthesis, ed. I. Marek, Wiley-VCH, Weinheim, Germany, 2002, pp. 1-49;
18. C. Zhao, J. Yan and Z. Xi, J. Org. Chem., 2003, 68, 4355-4360;
19. T. Takahashi, Z. Xi, Y. Nishihara, S. Huo, K. Kasai, K. Aoyagi, V. Denisov and E. Negishi, Tetrahedron, 1997, 53, 9123-9134.
20. (a) A. Goeke, D. Mertl and S. Jork, Chem. Commun., 2004, 166-167;
21. (b) H. Urabe, K. Mitsui, S. Ohta and F. Sato, J. Am. Chem. Soc., 2003, 125, 6074-6075.
22. (a) A. de Meijere, S. I. Kozhushkov and A. I. Savchenko, J. Organomet. Chem., 2004, 689, 2033-2055;
23. (b) A. de Meijere, S. I. Kozhushkov and A. I. Savchenko, in Titanium and Zirconium in Organic Synthesis, ed. I. Marek, Wiley-VCH, Weinheim, Germany, 2002, pp. 390-434.
24. C. M. Williams, V. Chaplinski, P. R. Schreiner and A. de Meijere, Tetrahedron Lett., 1998, 39, 7695-7698.
25. (a) P. Bertus and J. Szymoniak, Chem. Commun., 2001, 1792-1793;
26. (b) P. Bertus and J. Szymoniak, J. Org. Chem., 2002, 67, 3965-3968;
27. (c) P. Bertus and J. Szymoniak, Synlett, 2003, 265-267;
28. (d) C. Laroche, P. Bertus and J. Szymoniak, Tetrahedron Lett., 2003, 44, 2485-2487;
29. (e) P. Bertus and J. Szymoniak, J. Org. Chem., 2003, 68, 7133-7136.
30. Isopropyl and cyclohexyl Grignard reagents were used for an efficient ligand exchange in the syntheses of cyclopropanols and cyclopropylamines, see: F. Sato, H. Urabe and S. Okamoto, Chem. Rev., 2000, 100, 2835-2886;
31. J. Lee and J. K. Cha, J. Org. Chem., 1997, 62, 1584-1585;
32. A. de Meijere, C. M. Williams, A. Kourdioukov, S. V. Sviridov, V. Chaplinski, M. Kordes, A. I. Savchenko, C. Stratman and M. Noltenmeyer, Chem. Eur. J., 2002, 8, 3789-3801.
33. Cyclohexylmagnesium bromide, which was successfully used for intramolecular ligand-exchange with ω-unsaturated nitrites (ref. 9d), proved to be inefficient here.
34. 1-Substituted dienes did not afford the corresponding 3-cyclopentenyl amines under the conditions used here.
35. 3-Cyclopentenols were prepared from dienes and carboxylic esters by the use of activated Mg or electrochemically, see: R. D. Rieke, M. S. Sell and H. Xiong, J. Am. Chem. Soc., 1995, 117, 5429-5437;
36. T. Shono, M. Ishifune, H. Kinusaga and S. Kashimura, J. Org. Chem., 1992, 57, 5561-5563.