A theoretical investigation on the mechanism of the PtCl 2-mediated cycloisomerization of heteroatom-tethered 1,6-enynes

Journal of Organic Chemistry

Volumn 69, Issue 23, 2004, Pages 8018-8023

  Soriano, Elena ^a   Ballesteros, Paloma ^a   Marco Contelles, José ^b  

^a UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CALCULATIONS; CATALYSTS; ORGANIC COMPOUNDS; REACTION KINETICS;

ENYNES; HYDROGEN SHIFTS; MECHANISTIC STUDY;

PLATINUM COMPOUNDS;

CARBENOID; CYCLOPROPANE DERIVATIVE; CYCLOPROPYL PLATINA CARBENE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; CYCLOISOMERIZATION; ISOMERIZATION; SYNTHESIS;

EID: 8644286646     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048828h     Document Type: Article

References (39)

1. Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: New York, 2002.
2. (a) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16.
3. (b) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067-2096.
4. (c) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834.
5. (d) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215-236.
6. Ru(II): (a) Trost, B. M.; Indolese, A. G.; Mueller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615-623. (b) Trost, B. M.; Mueller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888-1899. (c) Nishida, M.; Adachi, N.; Onozuka, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158-9159. (d) Le Paih, J.; Rodriguez, D. C.; Derien, S.; Dixneuf, P. H. Synlett 2000, 95-97. (e) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714-715.
7. Ru(II): (a) Trost, B. M.; Indolese, A. G.; Mueller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615-623. (b) Trost, B. M.; Mueller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888-1899. (c) Nishida, M.; Adachi, N.; Onozuka, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158-9159. (d) Le Paih, J.; Rodriguez, D. C.; Derien, S.; Dixneuf, P. H. Synlett 2000, 95-97. (e) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714-715.
8. Ru(II): (a) Trost, B. M.; Indolese, A. G.; Mueller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615-623. (b) Trost, B. M.; Mueller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888-1899. (c) Nishida, M.; Adachi, N.; Onozuka, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158-9159. (d) Le Paih, J.; Rodriguez, D. C.; Derien, S.; Dixneuf, P. H. Synlett 2000, 95-97. (e) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714-715.
9. Ru(II): (a) Trost, B. M.; Indolese, A. G.; Mueller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615-623. (b) Trost, B. M.; Mueller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888-1899. (c) Nishida, M.; Adachi, N.; Onozuka, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158-9159. (d) Le Paih, J.; Rodriguez, D. C.; Derien, S.; Dixneuf, P. H. Synlett 2000, 95-97. (e) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714-715.
10. Ru(II): (a) Trost, B. M.; Indolese, A. G.; Mueller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615-623. (b) Trost, B. M.; Mueller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888-1899. (c) Nishida, M.; Adachi, N.; Onozuka, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158-9159. (d) Le Paih, J.; Rodriguez, D. C.; Derien, S.; Dixneuf, P. H. Synlett 2000, 95-97. (e) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714-715.
11. Rh(I): (f) Trost, B. M.; Lautens, M. Tetrahedron Lett. 1985, 26, 4887-4890. (g) Grigg, R.; Stevenson, P.; Worakun, T. Tetrahedron 1988, 44, 4967-4972. (h) Cao, P.; Wang, B.; Zhang, X. M. J. Am. Chem. Soc. 2000, 122, 6490-6491. (i) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249-252.
12. Rh(I): (f) Trost, B. M.; Lautens, M. Tetrahedron Lett. 1985, 26, 4887-4890. (g) Grigg, R.; Stevenson, P.; Worakun, T. Tetrahedron 1988, 44, 4967-4972. (h) Cao, P.; Wang, B.; Zhang, X. M. J. Am. Chem. Soc. 2000, 122, 6490-6491. (i) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249-252.
13. Rh(I): (f) Trost, B. M.; Lautens, M. Tetrahedron Lett. 1985, 26, 4887-4890. (g) Grigg, R.; Stevenson, P.; Worakun, T. Tetrahedron 1988, 44, 4967-4972. (h) Cao, P.; Wang, B.; Zhang, X. M. J. Am. Chem. Soc. 2000, 122, 6490-6491. (i) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249-252.
14. Rh(I): (f) Trost, B. M.; Lautens, M. Tetrahedron Lett. 1985, 26, 4887-4890. (g) Grigg, R.; Stevenson, P.; Worakun, T. Tetrahedron 1988, 44, 4967-4972. (h) Cao, P.; Wang, B.; Zhang, X. M. J. Am. Chem. Soc. 2000, 122, 6490-6491. (i) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249-252.
15. Pt(II): (j) Dankwardt, J. W. Tetrahedron Lett. 2001, 42, 5809-5812. (k) Martín-Matute, B.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2001, 40, 4754-4757. (l) Fürstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264-6267.
16. Pt(II): (j) Dankwardt, J. W. Tetrahedron Lett. 2001, 42, 5809-5812. (k) Martín-Matute, B.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2001, 40, 4754-4757. (l) Fürstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264-6267.
17. Pt(II): (j) Dankwardt, J. W. Tetrahedron Lett. 2001, 42, 5809-5812. (k) Martín-Matute, B.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2001, 40, 4754-4757. (l) Fürstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264-6267.
18. Ti(II): (m) Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976-1977.
19. Cr-Ni: (n) Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 5268-5270.
20. Co(I): (o) Buisine, O.; Aubert, C.; Malacria, M. Chem. Eur. J. 2001, 7, 3517-3525.
21. Blum, J.; Beerkraft, H.; Badrieh, Y. J. Org. Chem. 1995, 60, 5567-5569.
22. (a) Fürstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785-6786.
23. (b) Fürstner, A.; Stelzer F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869.
24. Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520.
25. A recent work suggesting the involvement of cyclopropylmetallacarbene in the formation of bicyclo[4.1.0]hept-4-enes: Nevado, C.; Cárdenas, D. J.; Echavarren, A. Chem. Eur. J. 2003, 9, 2627-2635.
26. 2.
27. The implication of related metallacarbenes as intermediates for the intramolecular cyclopropanation with alkenes has been previously proposed: (a) For Pt(II)-catalyzed processes: Mainetti, E.; Mouries, V.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. Angew. Chem., Int. Ed. 2002, 41, 2132-2135. (b) For rhodium salts and ruthenium carbonyl catalysts: Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104-9105.
28. The implication of related metallacarbenes as intermediates for the intramolecular cyclopropanation with alkenes has been previously proposed: (a) For Pt(II)-catalyzed processes: Mainetti, E.; Mouries, V.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. Angew. Chem., Int. Ed. 2002, 41, 2132-2135. (b) For rhodium salts and ruthenium carbonyl catalysts: Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104-9105.
29. Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241-2290.
30. For the forrmation of cyclopropane from metallacyclobutane structure, see: (a) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908-4916. (b) Van Koppen, P. A. M.; Jacobson, D. B.; Illies, A.; Bowers, M. T.; Hanratty, M.; Beauchamp, J. L. J. Am. Chem. Soc. 1989, 111, 1991-2001.
31. For the forrmation of cyclopropane from metallacyclobutane structure, see: (a) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908-4916. (b) Van Koppen, P. A. M.; Jacobson, D. B.; Illies, A.; Bowers, M. T.; Hanratty, M.; Beauchamp, J. L. J. Am. Chem. Soc. 1989, 111, 1991-2001.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.: Piskorz, P.; Komaromi, L.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M. P.; Gill, M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.03; Gaussian Inc.: Pittsburgh, PA, 2003.
33. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
34. (a) Lee, C.; Yang, W.; Parr, R. Phys. Rev. B 1988, 37, 785-789.
35. (b) Becke, A. J. Chem. Phys. 1993, 98, 5648-5652.
36. (a) Fukui, K. Acc. Chem. Res. 1981, 14, 363-368.
37. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
38. (a) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066-4073.
39. (b) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.