Ruthenium-catalyzed cycloisomerization of 1,6-enynes initiated by C-H activation [4]

Journal of the American Chemical Society

Volumn 121, Issue 41, 1999, Pages 9728-9729

  Trost, Barry M ^a   Toste, F Dean ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; RUTHENIUM;

CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CYCLIZATION; ISOMERISM; LETTER; MOLECULAR INTERACTION; REACTION ANALYSIS;

EID: 0032704430     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991977a     Document Type: Letter

References (24)

1. For reviews, see: Trost, B. M.; Krische, M. J. Synlett 1998, 1. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
2. For reviews, see: Trost, B. M.; Krische, M. J. Synlett 1998, 1. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
3. Pd: Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268 and references therein. Ru: Nishida, M.; Adachi, N. Onozuka, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158.
4. Pd: Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268 and references therein. Ru: Nishida, M.; Adachi, N. Onozuka, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158.
5. Pd: Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255 and references therein. Ti: Sturla, S. J.; Kabalaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976. Ni-Cr: Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 5268. Co: Kraft, M. E.; Wilson, A. M.; Dasse, O. A.; Bonaga, L. V. K.; Cheung, Y.Y.; Fu, Z.; Shao, B.; Scott, J. L. Tetrahedron Lett. 1998, 38, 5911. For related postulates, see: Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085 and references therein. Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104.
6. Pd: Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255 and references therein. Ti: Sturla, S. J.; Kabalaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976. Ni-Cr: Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 5268. Co: Kraft, M. E.; Wilson, A. M.; Dasse, O. A.; Bonaga, L. V. K.; Cheung, Y.Y.; Fu, Z.; Shao, B.; Scott, J. L. Tetrahedron Lett. 1998, 38, 5911. For related postulates, see: Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085 and references therein. Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104.
7. Pd: Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255 and references therein. Ti: Sturla, S. J.; Kabalaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976. Ni-Cr: Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 5268. Co: Kraft, M. E.; Wilson, A. M.; Dasse, O. A.; Bonaga, L. V. K.; Cheung, Y.Y.; Fu, Z.; Shao, B.; Scott, J. L. Tetrahedron Lett. 1998, 38, 5911. For related postulates, see: Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085 and references therein. Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104.
8. Pd: Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255 and references therein. Ti: Sturla, S. J.; Kabalaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976. Ni-Cr: Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 5268. Co: Kraft, M. E.; Wilson, A. M.; Dasse, O. A.; Bonaga, L. V. K.; Cheung, Y.Y.; Fu, Z.; Shao, B.; Scott, J. L. Tetrahedron Lett. 1998, 38, 5911. For related postulates, see: Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085 and references therein. Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104.
9. Pd: Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255 and references therein. Ti: Sturla, S. J.; Kabalaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976. Ni-Cr: Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 5268. Co: Kraft, M. E.; Wilson, A. M.; Dasse, O. A.; Bonaga, L. V. K.; Cheung, Y.Y.; Fu, Z.; Shao, B.; Scott, J. L. Tetrahedron Lett. 1998, 38, 5911. For related postulates, see: Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085 and references therein. Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104.
10. Pd: Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255 and references therein. Ti: Sturla, S. J.; Kabalaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976. Ni-Cr: Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 5268. Co: Kraft, M. E.; Wilson, A. M.; Dasse, O. A.; Bonaga, L. V. K.; Cheung, Y.Y.; Fu, Z.; Shao, B.; Scott, J. L. Tetrahedron Lett. 1998, 38, 5911. For related postulates, see: Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085 and references therein. Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104.
11. Pd: Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. Pt: Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901. Ru: Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049.
12. Pd: Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. Pt: Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901. Ru: Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049.
13. Pd: Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. Pt: Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901. Ru: Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049.
14. Ru: Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082.
15. (a) Cf.: Itoh, K.; Masuda, K.; Ikeda, H. Organometallics 1993, 12, 2752.
16. (b) However, such reactions are not common in Ru, see: Bennett, M. A.; Khan, K.; Wenger, E. In Comprehensive Organometallic Chemistry II; Shriver, D. F., Bruce, M. I., Eds.; Elsevier: New York, 1995; Vol. 7, Chapter 8, pp 509-511.
17. (c) Such reactions are common with Pd, see: Davies, J. A. In Comprehensive Organometallic Chemistry II; Shriver, D. F., Bruce, M. I., Eds.; Elsevier: New York, 1995; Vol. 9, Chapter 6, pp 331-340.
18. Trost, B. M.; Indolese, A.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615. Trost, B. M.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 615.
19. Trost, B. M.; Indolese, A.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615. Trost, B. M.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 615.
20. Trost, B. M.; Toste, F. D. Tetrahedron Lett., in press.
21. Gill, T. P.; Mann, K. R. Organometallics 1982, 1, 485.
22. This compound has been characterized spectroscopically and elemental composition established by high-resolution mass spectroscopy or combustion analysis.
23. The geometry of the enoate was established by NOEs as well as observed chemical shifts. It is not what would arise from a direct reductive elimination of the initial carbametalated intermediate. This geometry may derive by equilibration via the O-ruthenium enolate and faster reductive elimination of the alternate C-bond ruthenium enolate to give the more stable product.
24. For the intramolecular addition of π-allylpalladium and -nickel to alkynes, see: Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 1.2.