A titanium-catalyzed three-component coupling to generate α,β-unsaturated β-iminoamines

Journal of the American Chemical Society

Volumn 125, Issue 10, 2003, Pages 2880-2881

  Cao, Changsheng ^a   Shi, Yanhui ^a   Odom, Aaron L ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AMINE; BETA IMINOAMINE; LIGAND; METAL COMPLEX; PYRROLE DERIVATIVE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS;

EID: 0037433598     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0284714     Document Type: Article

References (41)

1. (a) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923-2924.
2. (b) Siebeneicher, H.; Doye, S. J. Prakt. Chem./Chem.-Ztg. 2000, 342, 102-106.
3. (c) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389-3391.
4. (d) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2001, 4411-4418.
5. (e) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967-3969.
6. (f) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839-2841.
7. (g) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475-1478.
8. (h) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213-1220.
9. (i) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961-1964.
10. (j) Haak, E.; Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2002. 457-463.
11. (k) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew. Chem., Int. Ed. 2002, 41, 2541-2543.
12. (l) Hill, J. E.; Profilet, R. D.; Fanwick, P. E.; Rothwell, I. P. Angew. Chem., Int. Ed. Engl. 1990, 29, 664-665.
13. Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853-2856.
14. For recent articles on multicomponent couplings, see: (a) Schreiber, S. L. Science 2000, 287, 1964-1969. (b) Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363. (c) Ding, S.; Gray, N. S.; Wu, X.; Ding, Q.; Schultz, P. G. J. Am. Chem. Soc. 2002, 124, 1594-1596. (d) Hsieh-Wilson, L. C.; Xiang, X.-D.; Schultz, P. G. Acc. Chem. Res. 1996, 29, 164-170. (e) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (f) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.-Eur. J. 2000, 6, 3321-3329. For some examples of transition metal-catalyzed three-component couplings, see: (g) Muraoka, T.; Kamiy, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284-1285 and references therein.
15. For recent articles on multicomponent couplings, see: (a) Schreiber, S. L. Science 2000, 287, 1964-1969. (b) Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363. (c) Ding, S.; Gray, N. S.; Wu, X.; Ding, Q.; Schultz, P. G. J. Am. Chem. Soc. 2002, 124, 1594-1596. (d) Hsieh-Wilson, L. C.; Xiang, X.-D.; Schultz, P. G. Acc. Chem. Res. 1996, 29, 164-170. (e) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (f) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.-Eur. J. 2000, 6, 3321-3329. For some examples of transition metal-catalyzed three-component couplings, see: (g) Muraoka, T.; Kamiy, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284-1285 and references therein.
16. For recent articles on multicomponent couplings, see: (a) Schreiber, S. L. Science 2000, 287, 1964-1969. (b) Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363. (c) Ding, S.; Gray, N. S.; Wu, X.; Ding, Q.; Schultz, P. G. J. Am. Chem. Soc. 2002, 124, 1594-1596. (d) Hsieh-Wilson, L. C.; Xiang, X.-D.; Schultz, P. G. Acc. Chem. Res. 1996, 29, 164-170. (e) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (f) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.-Eur. J. 2000, 6, 3321-3329. For some examples of transition metal-catalyzed three-component couplings, see: (g) Muraoka, T.; Kamiy, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284-1285 and references therein.
17. For recent articles on multicomponent couplings, see: (a) Schreiber, S. L. Science 2000, 287, 1964-1969. (b) Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363. (c) Ding, S.; Gray, N. S.; Wu, X.; Ding, Q.; Schultz, P. G. J. Am. Chem. Soc. 2002, 124, 1594-1596. (d) Hsieh-Wilson, L. C.; Xiang, X.-D.; Schultz, P. G. Acc. Chem. Res. 1996, 29, 164-170. (e) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (f) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.-Eur. J. 2000, 6, 3321-3329. For some examples of transition metal-catalyzed three-component couplings, see: (g) Muraoka, T.; Kamiy, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284-1285 and references therein.
18. For recent articles on multicomponent couplings, see: (a) Schreiber, S. L. Science 2000, 287, 1964-1969. (b) Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363. (c) Ding, S.; Gray, N. S.; Wu, X.; Ding, Q.; Schultz, P. G. J. Am. Chem. Soc. 2002, 124, 1594-1596. (d) Hsieh-Wilson, L. C.; Xiang, X.-D.; Schultz, P. G. Acc. Chem. Res. 1996, 29, 164-170. (e) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (f) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.-Eur. J. 2000, 6, 3321-3329. For some examples of transition metal-catalyzed three-component couplings, see: (g) Muraoka, T.; Kamiy, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284-1285 and references therein.
19. For recent articles on multicomponent couplings, see: (a) Schreiber, S. L. Science 2000, 287, 1964-1969. (b) Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363. (c) Ding, S.; Gray, N. S.; Wu, X.; Ding, Q.; Schultz, P. G. J. Am. Chem. Soc. 2002, 124, 1594-1596. (d) Hsieh-Wilson, L. C.; Xiang, X.-D.; Schultz, P. G. Acc. Chem. Res. 1996, 29, 164-170. (e) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (f) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.-Eur. J. 2000, 6, 3321-3329. For some examples of transition metal-catalyzed three-component couplings, see: (g) Muraoka, T.; Kamiy, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284-1285 and references therein.
20. For recent articles on multicomponent couplings, see: (a) Schreiber, S. L. Science 2000, 287, 1964-1969. (b) Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363. (c) Ding, S.; Gray, N. S.; Wu, X.; Ding, Q.; Schultz, P. G. J. Am. Chem. Soc. 2002, 124, 1594-1596. (d) Hsieh-Wilson, L. C.; Xiang, X.-D.; Schultz, P. G. Acc. Chem. Res. 1996, 29, 164-170. (e) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (f) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.-Eur. J. 2000, 6, 3321-3329. For some examples of transition metal-catalyzed three-component couplings, see: (g) Muraoka, T.; Kamiy, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284-1285 and references therein.
21. (a) Harris, S. A.; Ciszewski, J. T.; Odom, A. L. Inorg. Chem. 2001, 40, 1987-1988.
22. (b) Li, Y.; Turnas, A.; Ciszewski, J. T.; Odom, A. L. Inorg. Chem. 2002, 41, 6298.
23. (a) Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 5011-5013.
24. (b) Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2002, 21, 5148.
25. For examples, see: (a) Davis, T. L.; Yelland, W. E. J. Am. Chem. Soc. 1937, 59, 1998-1999.
26. (b) Saegusa, T.; Murase, I.; Ito, Y. J. Org. Chem. 1971, 36, 2876-2880.
27. (c) Bestchart, C.; Hegedus, L. S. J. Am. Chem. Soc. 1992, 114, 4, 5010-5017.
28. For mechanistic studies on group 4 metal-catalyzed hydroamination, see: (a) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632-4635. (b) Sweeney, Z. K.; Salsman, J. L.; Anderson, R. A.; Bergman, R. G. Angew. Chem., Int. Ed. 2000, 39, 2339-2343. (c) Polse, J. L.; Anderson, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 13405-13414. (d) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763. (e) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708-1719. (f) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305-2308.
29. For mechanistic studies on group 4 metal-catalyzed hydroamination, see: (a) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632-4635. (b) Sweeney, Z. K.; Salsman, J. L.; Anderson, R. A.; Bergman, R. G. Angew. Chem., Int. Ed. 2000, 39, 2339-2343. (c) Polse, J. L.; Anderson, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 13405-13414. (d) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763. (e) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708-1719. (f) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305-2308.
30. For mechanistic studies on group 4 metal-catalyzed hydroamination, see: (a) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632-4635. (b) Sweeney, Z. K.; Salsman, J. L.; Anderson, R. A.; Bergman, R. G. Angew. Chem., Int. Ed. 2000, 39, 2339-2343. (c) Polse, J. L.; Anderson, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 13405-13414. (d) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763. (e) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708-1719. (f) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305-2308.
31. For mechanistic studies on group 4 metal-catalyzed hydroamination, see: (a) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632-4635. (b) Sweeney, Z. K.; Salsman, J. L.; Anderson, R. A.; Bergman, R. G. Angew. Chem., Int. Ed. 2000, 39, 2339-2343. (c) Polse, J. L.; Anderson, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 13405-13414. (d) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763. (e) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708-1719. (f) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305-2308.
32. For mechanistic studies on group 4 metal-catalyzed hydroamination, see: (a) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632-4635. (b) Sweeney, Z. K.; Salsman, J. L.; Anderson, R. A.; Bergman, R. G. Angew. Chem., Int. Ed. 2000, 39, 2339-2343. (c) Polse, J. L.; Anderson, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 13405-13414. (d) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763. (e) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708-1719. (f) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305-2308.
33. For mechanistic studies on group 4 metal-catalyzed hydroamination, see: (a) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632-4635. (b) Sweeney, Z. K.; Salsman, J. L.; Anderson, R. A.; Bergman, R. G. Angew. Chem., Int. Ed. 2000, 39, 2339-2343. (c) Polse, J. L.; Anderson, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 13405-13414. (d) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763. (e) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708-1719. (f) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305-2308.
34. For recent examples of transition metal β-diketiminate chemistry, see: (a) Kakaliou, L.; Scanlon, W. J.; Qian, B.; Baek, S. W.; Smith, M. R., III; Motry, D. H. Inorg. Chem. 1999, 38, 5964-5977. (b) Fekl, U.; Goldberg, K. I. J. Am. Chem. Soc. 2002, 124, 6804-6805. (c) Spencer, D. J. E.; Aboelella, N. W.; Reynolds, A. M.; Holland, P. L.; Tolman, W. B. J. Am. Chem. Soc. 2002, 124, 2108-2109. (d) Smith, J. M.; Lachicotte, R. J.; Pittard, K. A.; Cundari, T. R.; Lukat-Rodgers, G.; Rodgers, K. R.; Holland, P. L. J. Am. Chem. Soc. 2001, 123, 9222-9223. (e) Dai, X.; Warren, T. H. Chem. Commun. 2001, 1998-1999. For a recent review: (f) Bourget-Merle, L.; Lappert, M. F.; Severn, J. R. Chem. Rev. 2002, 102, 3031.
35. For recent examples of transition metal β-diketiminate chemistry, see: (a) Kakaliou, L.; Scanlon, W. J.; Qian, B.; Baek, S. W.; Smith, M. R., III; Motry, D. H. Inorg. Chem. 1999, 38, 5964-5977. (b) Fekl, U.; Goldberg, K. I. J. Am. Chem. Soc. 2002, 124, 6804-6805. (c) Spencer, D. J. E.; Aboelella, N. W.; Reynolds, A. M.; Holland, P. L.; Tolman, W. B. J. Am. Chem. Soc. 2002, 124, 2108-2109. (d) Smith, J. M.; Lachicotte, R. J.; Pittard, K. A.; Cundari, T. R.; Lukat-Rodgers, G.; Rodgers, K. R.; Holland, P. L. J. Am. Chem. Soc. 2001, 123, 9222-9223. (e) Dai, X.; Warren, T. H. Chem. Commun. 2001, 1998-1999. For a recent review: (f) Bourget-Merle, L.; Lappert, M. F.; Severn, J. R. Chem. Rev. 2002, 102, 3031.
36. For recent examples of transition metal β-diketiminate chemistry, see: (a) Kakaliou, L.; Scanlon, W. J.; Qian, B.; Baek, S. W.; Smith, M. R., III; Motry, D. H. Inorg. Chem. 1999, 38, 5964-5977. (b) Fekl, U.; Goldberg, K. I. J. Am. Chem. Soc. 2002, 124, 6804-6805. (c) Spencer, D. J. E.; Aboelella, N. W.; Reynolds, A. M.; Holland, P. L.; Tolman, W. B. J. Am. Chem. Soc. 2002, 124, 2108-2109. (d) Smith, J. M.; Lachicotte, R. J.; Pittard, K. A.; Cundari, T. R.; Lukat-Rodgers, G.; Rodgers, K. R.; Holland, P. L. J. Am. Chem. Soc. 2001, 123, 9222-9223. (e) Dai, X.; Warren, T. H. Chem. Commun. 2001, 1998-1999. For a recent review: (f) Bourget-Merle, L.; Lappert, M. F.; Severn, J. R. Chem. Rev. 2002, 102, 3031.
37. For recent examples of transition metal β-diketiminate chemistry, see: (a) Kakaliou, L.; Scanlon, W. J.; Qian, B.; Baek, S. W.; Smith, M. R., III; Motry, D. H. Inorg. Chem. 1999, 38, 5964-5977. (b) Fekl, U.; Goldberg, K. I. J. Am. Chem. Soc. 2002, 124, 6804-6805. (c) Spencer, D. J. E.; Aboelella, N. W.; Reynolds, A. M.; Holland, P. L.; Tolman, W. B. J. Am. Chem. Soc. 2002, 124, 2108-2109. (d) Smith, J. M.; Lachicotte, R. J.; Pittard, K. A.; Cundari, T. R.; Lukat-Rodgers, G.; Rodgers, K. R.; Holland, P. L. J. Am. Chem. Soc. 2001, 123, 9222-9223. (e) Dai, X.; Warren, T. H. Chem. Commun. 2001, 1998-1999. For a recent review: (f) Bourget-Merle, L.; Lappert, M. F.; Severn, J. R. Chem. Rev. 2002, 102, 3031.
38. For recent examples of transition metal β-diketiminate chemistry, see: (a) Kakaliou, L.; Scanlon, W. J.; Qian, B.; Baek, S. W.; Smith, M. R., III; Motry, D. H. Inorg. Chem. 1999, 38, 5964-5977. (b) Fekl, U.; Goldberg, K. I. J. Am. Chem. Soc. 2002, 124, 6804-6805. (c) Spencer, D. J. E.; Aboelella, N. W.; Reynolds, A. M.; Holland, P. L.; Tolman, W. B. J. Am. Chem. Soc. 2002, 124, 2108-2109. (d) Smith, J. M.; Lachicotte, R. J.; Pittard, K. A.; Cundari, T. R.; Lukat-Rodgers, G.; Rodgers, K. R.; Holland, P. L. J. Am. Chem. Soc. 2001, 123, 9222-9223. (e) Dai, X.; Warren, T. H. Chem. Commun. 2001, 1998-1999. For a recent review: (f) Bourget-Merle, L.; Lappert, M. F.; Severn, J. R. Chem. Rev. 2002, 102, 3031.
39. For recent examples of transition metal β-diketiminate chemistry, see: (a) Kakaliou, L.; Scanlon, W. J.; Qian, B.; Baek, S. W.; Smith, M. R., III; Motry, D. H. Inorg. Chem. 1999, 38, 5964-5977. (b) Fekl, U.; Goldberg, K. I. J. Am. Chem. Soc. 2002, 124, 6804-6805. (c) Spencer, D. J. E.; Aboelella, N. W.; Reynolds, A. M.; Holland, P. L.; Tolman, W. B. J. Am. Chem. Soc. 2002, 124, 2108-2109. (d) Smith, J. M.; Lachicotte, R. J.; Pittard, K. A.; Cundari, T. R.; Lukat-Rodgers, G.; Rodgers, K. R.; Holland, P. L. J. Am. Chem. Soc. 2001, 123, 9222-9223. (e) Dai, X.; Warren, T. H. Chem. Commun. 2001, 1998-1999. For a recent review: (f) Bourget-Merle, L.; Lappert, M. F.; Severn, J. R. Chem. Rev. 2002, 102, 3031.
40. Boger, D. L.; Weinreb, S. N. Hetero Diels - Alder Methodology in Organic Synthesis. Academic Press: San Diego, 1987.
41. For a leading example, see: Brady, W. T.; Shieh, C. H. J. Org. Chem. 1983, 48, 2499-2502.