Change of the reaction pattern by methodological variations in a multicomponent assembly promoted by Ni complexes

Chemistry - A European Journal

Volumn 7, Issue 7, 2001, Pages 1503-1509

  García Gómez, Gabriel ^a   Moretó, Josep M ^a  

^a CSIC   (Spain)

Author keywords

Allyl complexes; Carbonylation; Cyclization; Nickel

Indexed keywords

ACETYLENE; COMPLEXATION; NICKEL;

CARBOMETALATION;

KETONES;

CHLOROTRIMETHYLSILANE; NICKEL COMPLEX;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; METAL BINDING; PROMOTER REGION; PROTEIN ASSEMBLY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0035312293     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010401)7:7<1503::AID-CHEM1503>3.0.CO;2-9     Document Type: Article

References (38)

1. a) B. M. Trost, Science 1991, 254, 1471-1477;
2. b) B. M. Trost, Angew. Chem. 1995, 107, 285-307;
3. Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281.
4. a) B. M. Trost, M. J. Krische, Synlett 1998, 1-16;
5. b) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-168;
6. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163;
7. c) I. Ojima, M. Tzamarioudaki, Z. Li, R. J. Donovan, Chem. Rev. 1996, 96, 635-662;
8. d) K. I. Booker-Milburn, A. Sharpe, J. Chem. Soc. Perkin Trans. 1 1998, 983-1005;
9. e) M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49-92.
10. For Pauson-Khand reactions see: a) O. Geis, U. G. Schmalz, Angew. Chem. 1998, 110, 955-958;
11. Angew. Chem. Int. Engl. 1998, 37, 911-915;
12. b) A. J. Fletcher, S. D. R. Christie, J. Chem. Soc. Perkin Trans. 1 2000, 1657-1668.
13. For three-component reactions see: a) T. Sambaiah, L.-P. Li, D.-J. Huang, C-H. Lin, D. K. Rayabarapu, C-H. Cheng, J. Org. Chem. 1999, 64, 3663-3670;
14. b) D.-M. Cui, N. Hashimoto, S. Ikeda, Y. Sato, J. Org. Chem. 1995, 60, 5752-5756;
15. c) B. M. Trost, A. B. Pinkerton, J. Am. Chem. Soc. 2000, 122, 8081-8082;
16. d) X. Qi, J. Montgomery, J. Org. Chem. 1999, 64, 9310-9313;
17. e) N. Chatani, M. Tobisu, T. Asaumi, S. Murai, Synthesis 2000 925-928;
18. f) H. Miao, Z. Yang, Org. Lett. 2000, 2, 1765-1768;
19. g) M. Kimura, K. Shibata, Y. Koudahashi, Y. Tamaru, Tetrahedron Lett. 2000, 41, 6789-6793, and references therein.
20. G. García-Gómez, J. M. Moretó, J. Am. Chem. Soc. 1999, 121, 878-879.
21. J. R. Johnson, P. S. Tully, P. B. Mackenzie, M. Sabat, J. Am. Chem. Soc. 1991, 113, 6172-6173.
22. a) S. Ikeda, N. Mori, Y. Sato, J. Am. Chem. Soc. 1997, 119, 4779-4780;
23. b) S. Ikeda, H. Watanabe, Y. Sato, J. Org. Chem. 1998, 63, 7026-7029;
24. c) N. Mori, S. Ikeda, Y. Sato, J. Am. Chem. Soc. 1999, 121, 2722-2727.
25. S. Ikeda, Y. Sato, J. Am. Chem. Soc. 1994, 116, 5975-5976.
26. a) F. Camps, J. Coll, J. M. Moretó, J. Torras, J. Org. Chem. 1989, 54, 1969-1978;
27. b) F. Camps, J. M. Moretó, Ll. Pagès, Tetrahedron 1992, 48, 3147-3162;
28. c) Ll. Pagès, A. Llebaria, F. Camps, E. Molins, C. Miravitlles, J. M. Moretó, J. Am. Chem. Soc. 1992, 114, 10449-10461.
29. a) J. Montgomery, J. Seo, H. M. P. Chui, Tetrahedron Lett. 1996, 37, 6839-6842;
30. b) D.-M. Cui, T. Tsuzuki, K. Miyake, S. Ikeda, Y. Sato, Tetrahedron 1998, 54, 1063-1072;
31. c) S. Ikeda, H. Miyashita, Y. Sato, Organometallics 1998, 17, 4316-4318.
32. Both alternative intramolecular 4-exo-trig and 5-endo-trig processes should be of high transition energy and, therefore, disfavoured.
33. D. Solé, Y. Cancho, A. Llebaria, J. M. Moretó, A. Delgado, J. Am. Chem. Soc. 1994, 116, 12133-12134.
34. T. Sambaiah, L.-P. Li, D.-J. Huang, C-H. Lin, D. K. Rayabarapu, C-H. Cheng, J. Org. Chem. 1999, 64, 3663-3670.
35. Recently, helical isomerism has been found in this type of compound when the vinyl substituents are large enough: S. Gréau, B. Radetich, T. V. RajanBabu, J. Am. Chem. Soc. 2000, 122, 8579-8580.
36. S. Ikeda, K. Kondo, Y. Sato, J. Org. Chem. 1996, 61, 8248-8255.
37. 4. If white rubber septa have been used, an indication of nickel carbonyl formation is a black stain on its internal surface. As a cautionary measure, we recommend working in an efficient fume hood and a cold trap (-80°C) should be inserted between the vacuum line and the evaporation flask. After the crude reaction mixture has reached dryness, the contents of the trap should be treated with iodine until the brown color remains.
38. Despite what was reported by Ikeda (S. Ikeda, H. Kondo, N. Mori, Chem. Comm. 2000, 815-816) we did not have any difficulties with this transformation.