A facile method for the synthesis of polycyclic indole derivatives: The generation and reaction of tungsten-containing azomethine ylides

Journal of the American Chemical Society

Volumn 124, Issue 39, 2002, Pages 11592-11593

  Kusama, Hiroyuki ^a   Takaya, Jun ^a   Iwasawa, Nobuharu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE YLIDE; INDOLE DERIVATIVE; TUNGSTEN;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; DISSOCIATION; ELECTRON TRANSPORT; REACTION ANALYSIS; STOICHIOMETRY; SYNTHESIS;

EID: 0037009990     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027589h     Document Type: Article

References (25)

1. For recent examples of metal-catalyzed indole syntheses, see: (a) Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113. (b) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000. 122, 5662 and references therein.
2. For recent examples of metal-catalyzed indole syntheses, see: (a) Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113. (b) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000. 122, 5662 and references therein.
3. For reviews on azomethine ylide, see: (a) Vedejs, E. Advances in Cycloaddition: JAI Press: Greenwich, CT, 1988; Vol. 1, pp 33-51. (b) Kanemaa, S.; Tsuge, O. Advances in Cycloaddition; JAI Press: Greenwich. CT, 1993: Vol. 3. pp 99-159. (c) Grigg, R.; Sridharan, V. Advances in Cycloaddition; JAI Press: Greenwich, CT, 1993; Vol. 3, pp 161-204. (d) Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 4. pp 1069-1109.
4. For reviews on azomethine ylide, see: (a) Vedejs, E. Advances in Cycloaddition: JAI Press: Greenwich, CT, 1988; Vol. 1, pp 33-51. (b) Kanemaa, S.; Tsuge, O. Advances in Cycloaddition; JAI Press: Greenwich. CT, 1993: Vol. 3. pp 99-159. (c) Grigg, R.; Sridharan, V. Advances in Cycloaddition; JAI Press: Greenwich, CT, 1993; Vol. 3, pp 161-204. (d) Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 4. pp 1069-1109.
5. For reviews on azomethine ylide, see: (a) Vedejs, E. Advances in Cycloaddition: JAI Press: Greenwich, CT, 1988; Vol. 1, pp 33-51. (b) Kanemaa, S.; Tsuge, O. Advances in Cycloaddition; JAI Press: Greenwich. CT, 1993: Vol. 3. pp 99-159. (c) Grigg, R.; Sridharan, V. Advances in Cycloaddition; JAI Press: Greenwich, CT, 1993; Vol. 3, pp 161-204. (d) Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 4. pp 1069-1109.
6. For reviews on azomethine ylide, see: (a) Vedejs, E. Advances in Cycloaddition: JAI Press: Greenwich, CT, 1988; Vol. 1, pp 33-51. (b) Kanemaa, S.; Tsuge, O. Advances in Cycloaddition; JAI Press: Greenwich. CT, 1993: Vol. 3. pp 99-159. (c) Grigg, R.; Sridharan, V. Advances in Cycloaddition; JAI Press: Greenwich, CT, 1993; Vol. 3, pp 161-204. (d) Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 4. pp 1069-1109.
7. For our results on the generation and reaction of metal-containing carbonyl ylides, see: Iwasawa, N.; Shido, M.; Kusama, H. J. Am. Chem. Soc. 2001, 123, 5814.
8. Initial cycloadduct 4a was a mixture of two diastereomers (1:1).
9. 5(thf) at room temperature to afford the same product 5a in 75% yield after 7 days.
10. For examples of electrophilic activation of alkynes with group 6 metals, including the formation of vinylidene complexes, see: (a) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687. (b) McDonald, F. E. Chem.-Eur. J. 1999, 5, 3103. (c) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749. (d) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260. (e) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518 and references therein.
11. For examples of electrophilic activation of alkynes with group 6 metals, including the formation of vinylidene complexes, see: (a) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687. (b) McDonald, F. E. Chem.-Eur. J. 1999, 5, 3103. (c) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749. (d) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260. (e) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518 and references therein.
12. For examples of electrophilic activation of alkynes with group 6 metals, including the formation of vinylidene complexes, see: (a) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687. (b) McDonald, F. E. Chem.-Eur. J. 1999, 5, 3103. (c) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749. (d) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260. (e) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518 and references therein.
13. For examples of electrophilic activation of alkynes with group 6 metals, including the formation of vinylidene complexes, see: (a) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687. (b) McDonald, F. E. Chem.-Eur. J. 1999, 5, 3103. (c) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749. (d) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260. (e) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518 and references therein.
14. For examples of electrophilic activation of alkynes with group 6 metals, including the formation of vinylidene complexes, see: (a) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687. (b) McDonald, F. E. Chem.-Eur. J. 1999, 5, 3103. (c) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749. (d) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260. (e) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518 and references therein.
15. Because the enamine moiety of the products 11 was fairly reactive as a dipolarophile, [3 + 2] cycloaddition between 11 and the ylide intermediate 2a also proceeded to give 2:1 cycloadducts (see Supporting Information).
16. For examples of Lewis acid-promoted, nucleophilic substitution reaction onto N.O-acetals, see: (a) Smith, A. B., III; Kanoh, N.; Ishiyama, H.; Hartz, R. A. J. Am. Chem. Soc. 2000, 122, 11254. (b) Sugiura, M.; Hagio, H.; Hirabayashi, R.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 12510 and references therein.
17. For examples of Lewis acid-promoted, nucleophilic substitution reaction onto N.O-acetals, see: (a) Smith, A. B., III; Kanoh, N.; Ishiyama, H.; Hartz, R. A. J. Am. Chem. Soc. 2000, 122, 11254. (b) Sugiura, M.; Hagio, H.; Hirabayashi, R.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 12510 and references therein.
18. The formation of formal [4 + 2] cycloadducts can be explained by Diels-Alder reaction of the ylide intermediate with tert-butyl vinyl ether.
19. For examples of the 1,2-migration of hydrogen or silicon groups in group 6 carbene complexes, see: (a) Dorwald, F. Z. Metal Carbenes in Organic Synthesis: Wiley-VCH: Weinheim, 1999. (b) Iwasawa, N.; Saitou, M.; kusama, H. J. Organomet. Chem. 2001, 617-618, 741 and references therein.
20. For examples of the 1,2-migration of hydrogen or silicon groups in group 6 carbene complexes, see: (a) Dorwald, F. Z. Metal Carbenes in Organic Synthesis: Wiley-VCH: Weinheim, 1999. (b) Iwasawa, N.; Saitou, M.; kusama, H. J. Organomet. Chem. 2001, 617-618, 741 and references therein.
21. 1,2-Alkyl migration of group 6 metal carbene intermediates is reported in a few, specific cases. See: (a) Zora, M.; Herndon, J. W.; Li, Y.; Rossi, J. Tetrahedron 2001, 57, 5097 and references therein. (b) Nagao, K.; Chiba, M.; Kim, S.-W. Synthesis 1983, 197.
22. 1,2-Alkyl migration of group 6 metal carbene intermediates is reported in a few, specific cases. See: (a) Zora, M.; Herndon, J. W.; Li, Y.; Rossi, J. Tetrahedron 2001, 57, 5097 and references therein. (b) Nagao, K.; Chiba, M.; Kim, S.-W. Synthesis 1983, 197.
23. For other examples of 1,2-alkyl migration in carbene complexes of the late transition metals, see ref 10a. See also: (a) Bly, R. S.; Bly, R. K.; Hossain, M. M.; Lebioda, L.; Raja, M. J. Am. Chem. Soc. 1988, 110, 7723.
24. For examples of the synthesis of mitomycin C and its analogues, see: (a) Remers, W. A.; Iyenger, B. S. Recent Prog. Chem. Synth. Antibiot. 1990, 415. (b) Michael, J. P.; Koning, C. B.; Petersen, R. L.; Stanbury, T. V. Tetrahedron Lett. 2001, 42, 7513 and references therein.
25. For examples of the synthesis of mitomycin C and its analogues, see: (a) Remers, W. A.; Iyenger, B. S. Recent Prog. Chem. Synth. Antibiot. 1990, 415. (b) Michael, J. P.; Koning, C. B.; Petersen, R. L.; Stanbury, T. V. Tetrahedron Lett. 2001, 42, 7513 and references therein.