Cyclobutene formation in PtCl2-catalyzed cycloisomerizations of heteroatom-tethered 1,6-enynes

Chemistry - A European Journal

Volumn 20, Issue 37, 2014, Pages 11703-11706

  Ni, Zhenjie ^a   Giordano, Laurent ^a   Tenaglia, Alphonse ^a  

^a AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

cyclobutenes; cycloisomerization; enynes; platinum; small ring systems; solvent effects

Indexed keywords

AMIDES; CATALYSIS; ISOMERIZATION; PLATINUM; PLATINUM COMPOUNDS; SOLVENTS;

CYCLOBUTENES; CYCLOISOMERIZATIONS; ENYNES; SMALL RING SYSTEMS; SOLVENT EFFECTS;

BUTENES;

EID: 84906946150     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201403643     Document Type: Article

References (50)

1. A. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478-3519
2. Angew. Chem. Int. Ed. 2007, 46, 3410-3449
3. A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211
4. L. Zhang, J. Sun, S. A. Kozmin, Adv. Synth. Catal. 2006, 348, 2271-2296
5. E. Carrero-Gomez, A. M. Echavarren, in Handbook of Cyclization Reactions (Ed.:, S. Ma,), Wiley-VCH, Weinheim, 2010, pp. 625-686.
6. streptorubinB and metacycloprodigiosin:, A. Fürstner, H. Szillat, B. Gabor, R. Mynott, J. Am. Chem. Soc. 1998, 120, 8305-8314
7. roseophilin:, B. M. Trost, G. A. Doherty, J. Am. Chem. Soc. 2000, 122, 3801-3810
8. jungianol:, A. S. K. Hashmi, L. Ding, J. W. Bats, P. Fischer, W. Frey, Chem. Eur. J. 2003, 9, 4339-4345
9. (+)-lycopladyneA:, S. T. Staben, J. J. Kennedy-Smith, D. Huang, B. K. Corkey, R. L. LaLonde, F. D. Toste, Angew. Chem. 2006, 118, 6137-6140
10. Angew. Chem. Int. Ed. 2006, 45, 5991-5994
11. nakadomarinA:, H. Deng, H. Yang, Z. Tong, Z. Li, H. Zhai, Org. Lett. 2008, 10, 1791-1793
12. ventricosene:, S. G. Sethofer, S. T. Staben, O. Y. Hung, F. D. Toste, Org. Lett. 2008, 10, 4315-4318
13. (+)-orientalolF and pubinernoidB:, E. Jiménez-Núñez, K. Molawi, A. M. Echavarren, Chem. Commun. 2009, 7327-7329
14. 9(12)-capnellene:, G. Lemière, V. Gandon, K. Cariou, A. Hours, T. Fukuyama, A.-L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2009, 131, 2993-3006
15. (-)-englerinA:, K. Molawi, N. Delpont, A. M. Echavarren, Angew. Chem. 2010, 122, 3595-3597
16. Angew. Chem. Int. Ed. 2010, 49, 3517-3519
17. P. Klahn, A. Duschek, C. Liébert, S. F. Kirsch, Org. Lett. 2012, 14, 1250-1253
18. see also:, F. Gagosz, in Modern Tools for the Synthesis of Complex Bioactive Molecules (Eds.:, J. Cossy, S. Arseniyadis,), Wiley, Hoboken, 2012, pp. 111-154.
19. E. Soriano, M. Marco-Contelles, Acc. Chem. Res. 2009, 42, 1026-1036
20. Topics in Current Chemistry, Vol.302: Computational Mechanisms of Au and Pt Catalyzed Reactions (Eds.:, E. Soriano, M. Marco-Contelles,), Springer, Berlin, 2011.
21. J. Blum, H. Beer-Krafts, Y. Badrieh, J. Org. Chem. 1995, 60, 5567-5569
22. N. Chatani, N. Furukawa, H. Sakurai, S. Murai, Organometallics 1996, 15, 901-903
23. A. Fürstner, H. Szillat, F. Stelzer, J. Am. Chem. Soc. 2000, 122, 6785-6786; gold catalysts
24. C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Càrdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456-2460
25. Angew. Chem. Int. Ed. 2004, 43, 2402-2406
26. C. Nieto-Oberhuber, M. P. Muñoz, S. Lõpez, E. Jiménez-Núñez, C. Nevado, E. Herrero-Gõmez, M. Raducan, A. M. Echavarren, Chem. Eur. J. 2006, 12, 1677-1693; < lit f>
27. S. I. Lee, S. M. Kim, S. Y. Kim, Y. K. Chung, Synlett 2006, 14, 2256-2260.
28. Y. T. Lee, Y. K. Kang, Y. K. Chung, J. Org. Chem. 2009, 74, 7922-7934.
29. J.-B. Xia, W.-B. Liu, T.-M. Wang, S.-L. You, Chem. Eur. J. 2010, 16, 6442-6446.
30. A. Tenaglia, S. Gaillard, Angew. Chem. 2008, 120, 2488-2491
31. Angew. Chem. Int. Ed. 2008, 47, 2454-2457
32. S. M. Stevenson, E. T. Newcomb, E. M. Ferreira, Chem. Commun. 2014, 50, 5239-5241
33. for a gold-catalyzed version, see:, A. Simonneau, Y. Harrak, L. Jeanne-Julien, G. Lemière, V. Mouriès-Mansuy, J.-P. Goddard, M. Malacria, L. Fensterbank, ChemCatChem 2013, 5, 1096-1099; for a review, see
34. B. Crone, S. F. Kirsch, Chem. Eur. J. 2008, 14, 3514-3522.
35. M. Mendez, V. Mamane, A. Fürstner, Chemtracts 2003, 16, 397-425
36. C. Bruneau, Angew. Chem. 2005, 117, 2380-2386
37. Angew. Chem. Int. Ed. 2005, 44, 2328-2334.
38. The structure of 2a was confirmed by X-ray diffraction analysis. CCDC-987528 (2a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
39. A. Fürstner, P. W. Davies, T. Gress, J. Am. Chem. Soc. 2005, 127, 8244-8245
40. A. Fürstner, P. W. Davies, J. Am. Chem. Soc. 2005, 127, 15024-15025
41. A. Fürstner, C. Aïssa, J. Am. Chem. Soc. 2006, 128, 6306-6307.
42. A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863-11869
43. C. Fernández-Rivas, M. Méndez, A. M. Echavarren, J. Am. Chem. Soc. 2000, 122, 1221-1222
44. C. Fernández-Rivas, M. Méndez, C. Nieto-Oberhuber, A. M. Echavarren, J. Org. Chem. 2002, 67, 5197-5201.
45. CCDC-987529 (2m) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
46. For coordination of DMA in ruthenium-catalyzed cycloisomerizations of 1,7-enynes, see:, B. M. Trost, A. C. Gutierrez, E. M. Ferreira, J. Am. Chem. Soc. 2010, 132, 9206-9218.
47. 2 at room temperature and readily releases DMA within 2min.
48. Location of platinum at the endo position of alkyne has been proposed for the cycloisomerization of ene-ynamides, see:, F. Marion, J. Coulomb, C. Courillon, L. Fensterbank, M. Malacria, Org. Lett. 2004, 6, 1509-1511.
49. P. A. Kramer, C. Masters, J. Chem. Soc. Dalton Trans. 1975, 849-852; hydrothermal conditions
50. M. Yamamoto, Y. Yokota, K. Oshima, S. Matsubara, Chem. Commun. 2004, 1714-1715.