Preparation of substituted cyclopentadienes through platinum(II)-catalyzed cyclization of 1,2,4-trienes

Angewandte Chemie - International Edition

Volumn 46, Issue 6, 2007, Pages 909-911

  Funami, Hideaki ^a   Kusama, Hiroyuki ^a   Iwasawa, Nobuharu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Allenes; Carbenes; Cyclopentadienes; Platinum; Synthetic methods

Indexed keywords

CATALYSIS; PLATINUM; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ALLENES; CARBENES; CYCLOPENTADIENES; SYNTHETIC METHODS;

AROMATIC COMPOUNDS;

ALKENE; CYCLOPENTANE DERIVATIVE; PLATINUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKENES; CATALYSIS; CYCLIZATION; CYCLOPENTANES; MOLECULAR STRUCTURE; PLATINUM; STEREOISOMERISM;

EID: 33846670579     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603986     Document Type: Article

References (41)

1. a) H. Yoon, W. Chae, Tetrahedron Lett. 1997, 38, 5169-5172, and references therein;
2. b) F. Fringuelli, A. Taticchi, The Diels-Alder Reaction: Selected Practical Methods, Wiley, New York, 2002.
3. a) R. L. Halterman, Chem. Rev. 1992, 92, 965-994;
4. b) A. Togni, R. L. Halterman, Metallocenes, Vol. 1, Wiley-VCH, Weinheim, 1996 and Vol. 2, 1998;
5. c) U. Siemeling, Chem. Rev. 2000, 100, 1495-1526.
6. a) V. Quindt, D. Saurenz, O. Schmitt, M. Schär, T. Dezember, G. Wolmershäuser, H. Sitzmann, J. Organomet. Chem. 1999, 579, 376-384, and references therein;
7. b) B. J. Rausch, R. Gleiter, F. Rominger, J. Organomet. Chem. 2002, 658, 242-250.
8. a) C. G. Venier, E. W. Casserly, J. Am. Chem. Soc. 1990, 112, 2808-2809;
9. b) Z. Duan, W.-H. Sun, Y. Liu, T. Takahashi, Tetrahedron Lett. 2000, 41, 7471-7474;
10. c) H. Fang, C. Zhao, G. Li, Z. Xi, Tetrahedron 2003, 59, 3779-3786, and references therein;
11. d) S. Zhou, B. Yan, Y. Liu, J. Org. Chem. 2005, 70, 4006-4012;
12. e) S. Datta, A. Odedra, R.-S. Liu, J. Am. Chem. Soc. 2005, 127, 11 606-11 607.
13. For the formation of carbocycles through the transition-metal-catalyzed electrophilic activation of allenes, see: a) T. Miura, K. Kiyota, H. Kusama, K. Lee, H. Kim, S. Kim, P. H. Lee, N. Iwasawa, Org. Lett. 2003, 5, 1725-1728;
14. b) L. Zhang, J. Am. Chem. Soc. 2005, 127, 16 804-16 805;
15. c) N. Marion, S. Díez-González, P. de Frémont, A. R. Noble, S. P. Nolan, Angew. Chem. 2006, 118, 3729-3732;
16. Angew. Chem. Int. Ed. 2006, 45, 3647-3650;
17. d) L. Zhang, S. Wang, J. Am. Chem. Soc. 2006, 128, 1442-1443;
18. e) A. Buzas, F. Gagosz, J. Am. Chem. Soc. 2006, 128, 12 614-12 615.
19. a) R. W. Bates, V. Satcharoen, Chem. Soc. Rev. 2002, 31, 12-21;
20. b) S. Ma, Chem. Rev. 2005, 105, 2829-2871.
21. For the platinum(II)-catalyzed electrophilic activation of allenes, see: Z. Zhang, C. Liu, R. E. Kinder, X. Han, H. Qian, R. A. Widenhoefer, J. Am. Chem. Soc. 2006, 128, 9066-9073.
22. For recent reviews on platinum(II)-catalyzed reactions, see: a) M. Méndez, V. Mamane, A. Fürstner, Chemtracts 2003, 16, 397-425;
23. b) A. M. Echavarren, C. Nevado, Chem. Soc. Rev. 2004, 33, 431-436.
24. 1,2,4-Trienes 1 were readily prepared in three steps [Eq. (2); Ms = methanesulfonyl]. See Supporting Information for details. (Chemical Equation Presented)
25. For the determination of platinum(II)-π-complexed allenes, see: P. Salvadori, G. Uccello-Barretta, R. Lazzaroni, A. M. Caporusso, J. Chem. Soc. Chem. Commun. 1990, 1121-1123.
26. A related pentadienyl cationic intermediate is proposed in the gold(I)-catalyzed reaction of enynyl actates; see: a) Ref. [5b-d];
27. b) X. Shi, D. J. Gorin, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 5802-5803.
28. For a gold(I)-catalyzed tandem cycloisomerization/ring-enlargement process with 1,5-enynes, see: M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10 858-10 859.
29. For other examples of 1,2-alkyl migrations of platinum-carbene intermediates, see: a) H. Kusama, H. Funami, J. Takaya, N. Iwasawa, Org. Lett. 2004, 6, 605-608;
30. b) H. Kusama, Y. Miyashita, J. Takaya, N. Iwasawa, Org. Lett. 2006, 8, 289-292;
31. c) J. Sun, M. P. Conley, L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2006, 128, 9705-9710;
32. d) C. Nieto-Oberhuber, S. López, E. Jiménez- Núñez, A. M. Echavarren, Chem. Eur. J. 2006, 12, 5916-5923, and references therein.
33. The presence of the cyclopropane ring was confirmed mainly on the basis of the presence of geminal protons in a highfield region (δ = -0.1-0.6 ppm) with a small geminal coupling constant (J = 3.2 Hz), features that are characteristic of cyclopropane derivatives. The structure was further confirmed by HMBC and differential NOE spectra. See Supporting Information for details of the assignment.
34. a) P. Yates, S. Danishefsky, J. Am. Chem. Soc. 1962, 84, 879-880;
35. b) J. Wrobel, K. Takahashi, V. Honkan, G. Lannoye, J. M. Cook, S. H. Bertz, J. Org. Chem. 1983, 48, 139-141;
36. c) H. Kusama, H. Yamabe, Y. Onizawa, T. Hoshino, N. Iwasawa, Angew. Chem. 2005, 117, 472-474;
37. Angew. Chem. Int. Ed. 2005, 44, 468-470;
38. d) W. Shi, B. Zhang, J. Zhang, B. Liu, S. Zhang, J. Wang, Org. Lett. 2005, 7, 3103-3106.
39. For platinum-carbene intermediates, see: a) N. Chatani, N. Furukawa, H. Sakurai, S. Murai, Organometallics 1996, 15, 901-903;
40. b) B. Martín-Matute, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2003, 125, 5757-5766;
41. c) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654-8655.