AuBr3- and Cu(OTf)2-catalyzed intramolecular [4 + 2] cycloaddition of tethered alkynyl and alkenyl enynones and enynals: A new synthetic method for functionalized polycyclic hydrocarbons

Journal of Organic Chemistry

Volumn 70, Issue 9, 2005, Pages 3682-3685

  Asao, Naoki ^a   Sato, Kenichiro ^a   Menggenbateer, ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; CHEMICAL BONDS; COPPER; DERIVATIVES; GOLD COMPOUNDS; KETONES; MOLECULAR DYNAMICS;

CARBONYL GROUP; INTERMOLECULAR CYCLOADDITION; LEWIS ACIDS; NEUCLEOPHILIC ADDITION;

POLYCYCLIC AROMATIC HYDROCARBONS;

ALKENYL GROUP; ALKYNYL GROUP; BROMIDE; CARBON; CARBONYL DERIVATIVE; COPPER; DIHYDRONAPHTHYL KETONE; GOLD; KETONE DERIVATIVE; LEWIS ACID; NAPHTHYL GROUP; POLYCYCLIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; DIELS ALDER REACTION; ELECTRON; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 17744383592     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0500434     Document Type: Article

References (37)

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16. For recent examples for naphthalene syntheses, see: (a) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226-10227. (b) Wakasugi, K.; Nishi, Y.; Tanabe, Y. Tetrahedron Lett. 2000, 41, 5937-5942. (c) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518-519. (d) Huang, Q.; Larock, R. C. Org. Lett. 2002, 4, 2505-2508. (e) Viswanathan, G. S.; Wang, M.; Li, C.-J. Angew. Chem., Int. Ed. 2002, 41, 2138-2141. (f) Yasukawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 12680-12681. (g) Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553-1555. (h) Ramakrishna, T. V. V.; Sharp, P. R. Org. Lett. 2003, 5, 877-879. (i) Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; Gonzalez, J. M. Org. Lett. 2003, 5, 4121-4123. (j) Shen, H.-C.; Pal, S.; Lian, J.-J.; Liu, R.-S. J. Am. Chem. Soc. 2003, 125, 15762-15763. (k) Kusama, H.; Funami, H.; Takaya, J.; Iwasawa, N. Org. Lett. 2004, 6, 605-608.
17. For recent examples for naphthalene syntheses, see: (a) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226-10227. (b) Wakasugi, K.; Nishi, Y.; Tanabe, Y. Tetrahedron Lett. 2000, 41, 5937-5942. (c) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518-519. (d) Huang, Q.; Larock, R. C. Org. Lett. 2002, 4, 2505-2508. (e) Viswanathan, G. S.; Wang, M.; Li, C.-J. Angew. Chem., Int. Ed. 2002, 41, 2138-2141. (f) Yasukawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 12680-12681. (g) Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553-1555. (h) Ramakrishna, T. V. V.; Sharp, P. R. Org. Lett. 2003, 5, 877-879. (i) Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; Gonzalez, J. M. Org. Lett. 2003, 5, 4121-4123. (j) Shen, H.-C.; Pal, S.; Lian, J.-J.; Liu, R.-S. J. Am. Chem. Soc. 2003, 125, 15762-15763. (k) Kusama, H.; Funami, H.; Takaya, J.; Iwasawa, N. Org. Lett. 2004, 6, 605-608.
18. For recent examples for naphthalene syntheses, see: (a) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226-10227. (b) Wakasugi, K.; Nishi, Y.; Tanabe, Y. Tetrahedron Lett. 2000, 41, 5937-5942. (c) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518-519. (d) Huang, Q.; Larock, R. C. Org. Lett. 2002, 4, 2505-2508. (e) Viswanathan, G. S.; Wang, M.; Li, C.-J. Angew. Chem., Int. Ed. 2002, 41, 2138-2141. (f) Yasukawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 12680-12681. (g) Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553-1555. (h) Ramakrishna, T. V. V.; Sharp, P. R. Org. Lett. 2003, 5, 877-879. (i) Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; Gonzalez, J. M. Org. Lett. 2003, 5, 4121-4123. (j) Shen, H.-C.; Pal, S.; Lian, J.-J.; Liu, R.-S. J. Am. Chem. Soc. 2003, 125, 15762-15763. (k) Kusama, H.; Funami, H.; Takaya, J.; Iwasawa, N. Org. Lett. 2004, 6, 605-608.
19. For recent examples for naphthalene syntheses, see: (a) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226-10227. (b) Wakasugi, K.; Nishi, Y.; Tanabe, Y. Tetrahedron Lett. 2000, 41, 5937-5942. (c) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518-519. (d) Huang, Q.; Larock, R. C. Org. Lett. 2002, 4, 2505-2508. (e) Viswanathan, G. S.; Wang, M.; Li, C.-J. Angew. Chem., Int. Ed. 2002, 41, 2138-2141. (f) Yasukawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 12680-12681. (g) Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553-1555. (h) Ramakrishna, T. V. V.; Sharp, P. R. Org. Lett. 2003, 5, 877-879. (i) Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; Gonzalez, J. M. Org. Lett. 2003, 5, 4121-4123. (j) Shen, H.-C.; Pal, S.; Lian, J.-J.; Liu, R.-S. J. Am. Chem. Soc. 2003, 125, 15762-15763. (k) Kusama, H.; Funami, H.; Takaya, J.; Iwasawa, N. Org. Lett. 2004, 6, 605-608.
20. For recent examples for naphthalene syntheses, see: (a) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226-10227. (b) Wakasugi, K.; Nishi, Y.; Tanabe, Y. Tetrahedron Lett. 2000, 41, 5937-5942. (c) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518-519. (d) Huang, Q.; Larock, R. C. Org. Lett. 2002, 4, 2505-2508. (e) Viswanathan, G. S.; Wang, M.; Li, C.-J. Angew. Chem., Int. Ed. 2002, 41, 2138-2141. (f) Yasukawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 12680-12681. (g) Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553-1555. (h) Ramakrishna, T. V. V.; Sharp, P. R. Org. Lett. 2003, 5, 877-879. (i) Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; Gonzalez, J. M. Org. Lett. 2003, 5, 4121-4123. (j) Shen, H.-C.; Pal, S.; Lian, J.-J.; Liu, R.-S. J. Am. Chem. Soc. 2003, 125, 15762-15763. (k) Kusama, H.; Funami, H.; Takaya, J.; Iwasawa, N. Org. Lett. 2004, 6, 605-608.
21. For recent examples for naphthalene syntheses, see: (a) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226-10227. (b) Wakasugi, K.; Nishi, Y.; Tanabe, Y. Tetrahedron Lett. 2000, 41, 5937-5942. (c) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518-519. (d) Huang, Q.; Larock, R. C. Org. Lett. 2002, 4, 2505-2508. (e) Viswanathan, G. S.; Wang, M.; Li, C.-J. Angew. Chem., Int. Ed. 2002, 41, 2138-2141. (f) Yasukawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 12680-12681. (g) Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553-1555. (h) Ramakrishna, T. V. V.; Sharp, P. R. Org. Lett. 2003, 5, 877-879. (i) Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; Gonzalez, J. M. Org. Lett. 2003, 5, 4121-4123. (j) Shen, H.-C.; Pal, S.; Lian, J.-J.; Liu, R.-S. J. Am. Chem. Soc. 2003, 125, 15762-15763. (k) Kusama, H.; Funami, H.; Takaya, J.; Iwasawa, N. Org. Lett. 2004, 6, 605-608.
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25. For recent examples for 1,2-dihydronaphthalene syntheses, see: (a) Ahmed, A.; Clayden, J.; Rowley, M. Synlett 1999, 1954-1956. (b) Shindo, M.; Koga, K.; Asano, Y.; Tomioka, K. Tetrahedron 1999, 55, 4955-4968. (c) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (d) Inoue, H.; Chatani, N.; Murai, S. J. Org. Chem. 2002, 67, 1414-1417.
26. For recent examples for 1,2-dihydronaphthalene syntheses, see: (a) Ahmed, A.; Clayden, J.; Rowley, M. Synlett 1999, 1954-1956. (b) Shindo, M.; Koga, K.; Asano, Y.; Tomioka, K. Tetrahedron 1999, 55, 4955-4968. (c) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (d) Inoue, H.; Chatani, N.; Murai, S. J. Org. Chem. 2002, 67, 1414-1417.
27. For recent examples for 1,2-dihydronaphthalene syntheses, see: (a) Ahmed, A.; Clayden, J.; Rowley, M. Synlett 1999, 1954-1956. (b) Shindo, M.; Koga, K.; Asano, Y.; Tomioka, K. Tetrahedron 1999, 55, 4955-4968. (c) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918. (d) Inoue, H.; Chatani, N.; Murai, S. J. Org. Chem. 2002, 67, 1414-1417.
28. For examples, see: (a) Yagi, A.; Takeo, S. Yakugaku Zasshi 2003, 123, 517-532. (b) Takatsuki, A.; Sekino, Y.; Kadono, T.; Wakayama, S. Jpn. Kokai Tokkyo Koho 11171765 A2 19990629, 1999.
29. For examples, see: (a) Yagi, A.; Takeo, S. Yakugaku Zasshi 2003, 123, 517-532. (b) Takatsuki, A.; Sekino, Y.; Kadono, T.; Wakayama, S. Jpn. Kokai Tokkyo Koho 11171765 A2 19990629, 1999.
30. Dyker reported one example of the intramolecular acylnaphthalene sysnthesis using bialkynylbenzil as the starting material; see: Dyker, G.; Stirner, W.; Henkel, G.; Kockerling, M. Tetrahedron Lett. 1999, 40, 7457-7458.
31. For reviews on the gold catalyst, see: (a) Dyker, G. Angew. Chem., Int. Ed. 2000, 39, 4237-4239. (b) Hashmi, A. S. K. Gold Bull. 2003, 36, 3-9.
32. For reviews on the gold catalyst, see: (a) Dyker, G. Angew. Chem., Int. Ed. 2000, 39, 4237-4239. (b) Hashmi, A. S. K. Gold Bull. 2003, 36, 3-9.
33. Gold-catalyzed benzannulation, see: (a) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553-11554. (b) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. Org. Lett. 2001, 3, 3769-3771. (c) Dankwardt, J. W. Tetrahedron Lett. 2001, 42, 5809-5812. (d) Hashmi, A. S. K; Frost, T. M.; Bats, J. W. Catal. Today 2002, 72, 19-27.
34. Gold-catalyzed benzannulation, see: (a) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553-11554. (b) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. Org. Lett. 2001, 3, 3769-3771. (c) Dankwardt, J. W. Tetrahedron Lett. 2001, 42, 5809-5812. (d) Hashmi, A. S. K; Frost, T. M.; Bats, J. W. Catal. Today 2002, 72, 19-27.
35. Gold-catalyzed benzannulation, see: (a) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553-11554. (b) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. Org. Lett. 2001, 3, 3769-3771. (c) Dankwardt, J. W. Tetrahedron Lett. 2001, 42, 5809-5812. (d) Hashmi, A. S. K; Frost, T. M.; Bats, J. W. Catal. Today 2002, 72, 19-27.
36. Gold-catalyzed benzannulation, see: (a) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553-11554. (b) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. Org. Lett. 2001, 3, 3769-3771. (c) Dankwardt, J. W. Tetrahedron Lett. 2001, 42, 5809-5812. (d) Hashmi, A. S. K; Frost, T. M.; Bats, J. W. Catal. Today 2002, 72, 19-27.
37. [3 + 2] cycloaddition of 16 with alkyne was proposed as another possible mechanism for the intermolecular benzannulation; see: Straub, B. F. Chem. Commun. 2004, 1726-1728.