Transition-metal-based Lewis acid and base ambiphilic catalysts of iridium hydride complexes: Multicomponent synthesis of glutarimides

Angewandte Chemie - International Edition

Volumn 42, Issue 28, 2003, Pages 3302-3304

  Takaya, Hikaru ^a   Yoshida, Kazunori ^a   Isozaki, Katsuhiro ^a   Terai, Hiroki ^a   Murahashi, Shun Ichi ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Ambiphilic catalyst; C H activation; Glutarimide; Iridium; Multicomponent reactions

Indexed keywords

DRUG PRODUCTS; IRIDIUM COMPOUNDS; OLEFINS;

LEWIS ACID;

CATALYSTS;

ALKENE; BASE; GLUTARIMIDE DERIVATIVE; IRIDIUM; LEWIS ACID; METAL DERIVATIVE; NITRILE;

ARTICLE; CATALYST; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0043269708     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351689     Document Type: Article

References (34)

1. a) S.-I. Murahashi, T. Naota, Bull. Chem. Soc. Jpn. 1996, 69, 1805;
2. b) S.-I. Murahashi, H. Takaya, Acc. Chem. Res. 2000, 33, 225.
3. B. Bosnich, Aldrichimica Acta 1998, 31, 76.
4. a) J. W. Faller, C. J. Smart, Tetrahedron Lett. 1989, 30, 1189;
5. b) W. Odenkirk, A. L. Rheingold, B. Bosnich, J. Am. Chem. Soc. 1992, 114, 6392;
6. c) E. P. Kündig, C. M. Saudan, G. Bernardinelli, Angew. Chem. Int. Ed. 1999, 38, 1220.
7. S.-I. Murahashi, T. Naota, E. Saito, J. Am. Chem. Soc. 1986, 108, 7846.
8. a) T. Naota, H. Taki, M. Mizuno, S.-I. Murahashi, J. Am. Chem. Soc. 1989, 111, 5954;
9. b) S.-I. Murahashi, T. Naota, H. Taki, M. Mizuno, H. Takaya, S. Komiya, Y. Mizuho, N. Oyasato, M. Hiraoka, M. Hirano, A. Fukuoka, J. Am. Chem. Soc. 1995, 117, 12436.
10. Our difinition of ambiphilic catalyst is a single redox catalyst used as either a Lewis acid or base under neutral conditions. Such catalyst is different from ambiphilic reagents and intermediates that function alternatively as nucleophiles and electrophiles. See, a) L. S. Hegedus, M. S. Holden, J. Org. Chem. 1985, 50, 3920; b) B. A. Andersen, H. F. Sleiman, A. K. Chang, L. M. White, J. Am. Chem. Soc. 1991, 113, 4871; c) T. Kondo, H. Ono, N. Satake, T. Mitsudo, Y. Watanabe, Organometallics 1995, 14, 1945; d) H. Nakamura, J.-G. Shim, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8113.
11. Our difinition of ambiphilic catalyst is a single redox catalyst used as either a Lewis acid or base under neutral conditions. Such catalyst is different from ambiphilic reagents and intermediates that function alternatively as nucleophiles and electrophiles. See, a) L. S. Hegedus, M. S. Holden, J. Org. Chem. 1985, 50, 3920; b) B. A. Andersen, H. F. Sleiman, A. K. Chang, L. M. White, J. Am. Chem. Soc. 1991, 113, 4871; c) T. Kondo, H. Ono, N. Satake, T. Mitsudo, Y. Watanabe, Organometallics 1995, 14, 1945; d) H. Nakamura, J.-G. Shim, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8113.
12. Our difinition of ambiphilic catalyst is a single redox catalyst used as either a Lewis acid or base under neutral conditions. Such catalyst is different from ambiphilic reagents and intermediates that function alternatively as nucleophiles and electrophiles. See, a) L. S. Hegedus, M. S. Holden, J. Org. Chem. 1985, 50, 3920; b) B. A. Andersen, H. F. Sleiman, A. K. Chang, L. M. White, J. Am. Chem. Soc. 1991, 113, 4871; c) T. Kondo, H. Ono, N. Satake, T. Mitsudo, Y. Watanabe, Organometallics 1995, 14, 1945; d) H. Nakamura, J.-G. Shim, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8113.
13. Our difinition of ambiphilic catalyst is a single redox catalyst used as either a Lewis acid or base under neutral conditions. Such catalyst is different from ambiphilic reagents and intermediates that function alternatively as nucleophiles and electrophiles. See, a) L. S. Hegedus, M. S. Holden, J. Org. Chem. 1985, 50, 3920; b) B. A. Andersen, H. F. Sleiman, A. K. Chang, L. M. White, J. Am. Chem. Soc. 1991, 113, 4871; c) T. Kondo, H. Ono, N. Satake, T. Mitsudo, Y. Watanabe, Organometallics 1995, 14, 1945; d) H. Nakamura, J.-G. Shim, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8113.
14. M. Rubiralta, E. Giralt, A. Diez in Piperidine, Elsevier, Amsterdam, 1991, Chap. 9, and references therein.
15. H. Takaya, T. Naota, S.-I. Murahashi, J. Am. Chem. Soc. 1998, 120, 4244.
16. C-H activations by iridium complexes see also, a) B. A. Anderson, R. G. Bergman, T. Mobley, T. H. Peterson, Acc. Chem. Res. 1995, 28, 154, and references therein; b) H. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995; c) E Liu, E. B. Pak, B. Singh, C. M. Jensen, A. S. Goldman, J. Am. Chem. Soc. 1999, 121, 4086.
17. C-H activations by iridium complexes see also, a) B. A. Anderson, R. G. Bergman, T. Mobley, T. H. Peterson, Acc. Chem. Res. 1995, 28, 154, and references therein; b) H. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995; c) E Liu, E. B. Pak, B. Singh, C. M. Jensen, A. S. Goldman, J. Am. Chem. Soc. 1999, 121, 4086.
18. C-H activations by iridium complexes see also, a) B. A. Anderson, R. G. Bergman, T. Mobley, T. H. Peterson, Acc. Chem. Res. 1995, 28, 154, and references therein; b) H. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995; c) E Liu, E. B. Pak, B. Singh, C. M. Jensen, A. S. Goldman, J. Am. Chem. Soc. 1999, 121, 4086.
19. a) D. Michalska, B. Morzyk, D. C. Bienko, W. Wojciechowski, Med. Hypotheses 2000, 54, 472;
20. b) J. M. Jacobson, Expert. Opin. Pharmacother. 2000, 1, 849.
21. R. W. Hartmann, B. Christine, J. Med. Chem. 1986, 29, 1362.
22. R. R. Goehring, T. D. Greenwood, G. C. Nwokogu, J. S. Pisipati, T. G. Rogers, J. F. Wolfe, J. Med. Chem. 1990, 33, 926.
23. S.-I. Murahashi, S. Sasao, E. Saito, T. Naota, J. Org. Chem. 1992, 57, 2521.
24. The stereochemistries of 9a and 9b were unequivocally determined by X-ray crystal structure analysis.
25. The stereochemistry of 11 was determined by NOE and NOESY experiments.
26. a) T. Naota, A. Tannna, S.-I. Murahashi, J. Am. Chem. Soc. 2000, 122, 2960;
27. b) T. Naota, A. Tannna, S. Kamuro, S.-I. Murahashi, J. Am. Chem. Soc. 2002, 124, 6842 and reference therein.
28. a) Y. Mizuho, N. Kasuga, S. Komiya, Chem. Lett. 1991, 2127;
29. b) M. Hirano, S. Kiyota, M. Imoto, S. Komiya, Chem. Commun. 2000, 1679.
30. T. Naota, A. Tannna, S.-I. Murahashi, Chem. Commun. 2001, 63.
31. 13C NMR chemical shifts shifted to extremely lower magnetic field (about 149 ppm), indicating high reactivity of the C≡N group of iridium complexes towards water.
32. The iridium-catalyzed reaction of 4-cyano-4-phenylpentanamide and water gave 2-methyl-2-phenylglutarimide in 99% yield.
33. The iridium-catalyzed Michael addition proceeds nonstereoselectively, but the iridium-catalyzed cyclocondensation of 3-methyl-2-(phenylsulfonyl)-pentanedinitrile proceeds with high diastereoselevtivity (9 a:10 a= 96:4).
34. H. Takaya, S.-I. Murahashi, Synlett, 2001, 991.