Rhodium-catalyzed asymmetric arylation of imines with organostannanes. Asymmetric synthesis of diarylmethylamines [14]

Journal of the American Chemical Society

Volumn 122, Issue 5, 2000, Pages 976-977

  Hayashi, Tamio ^a   Ishigedani, Mitsuo ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; METHYLAMINE; ORGANOTIN COMPOUND; RHODIUM; SULFONAMIDE;

CATALYSIS; CATALYST; ENANTIOMER; LETTER; LIGAND BINDING; POLYMERIZATION; SYNTHESIS;

EID: 0034624432     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9927220     Document Type: Letter

References (29)

1. For examples: (a) Bishop, M. J.; McNutt, R. W. Bioorg. Med. Chem. Lett. 1995, 5, 1311. (b) Spencer, C. M.; Foulds, D.; Peters, D. H. Drugs 1993, 46, 1055. (c) Sakurai, S.; Ogawa, N.; Suzuki, T.; Kato, K.; Ohashi, T.; Yasuda, S.; Kato, H.; Ito, Y. Chem. Pharm. Bull. 1996, 44, 765.
2. For examples: (a) Bishop, M. J.; McNutt, R. W. Bioorg. Med. Chem. Lett. 1995, 5, 1311. (b) Spencer, C. M.; Foulds, D.; Peters, D. H. Drugs 1993, 46, 1055. (c) Sakurai, S.; Ogawa, N.; Suzuki, T.; Kato, K.; Ohashi, T.; Yasuda, S.; Kato, H.; Ito, Y. Chem. Pharm. Bull. 1996, 44, 765.
3. For examples: (a) Bishop, M. J.; McNutt, R. W. Bioorg. Med. Chem. Lett. 1995, 5, 1311. (b) Spencer, C. M.; Foulds, D.; Peters, D. H. Drugs 1993, 46, 1055. (c) Sakurai, S.; Ogawa, N.; Suzuki, T.; Kato, K.; Ohashi, T.; Yasuda, S.; Kato, H.; Ito, Y. Chem. Pharm. Bull. 1996, 44, 765.
4. For recent examples of asymmetric synthesis of diarylmethylamines: (a) Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1996, 37, 4837. (b) Delorme, D.; Berthelette, C.; Lavoie, R.; Roberts, E. Tetrahedron Asym. 1998, 9, 3963. (c) Pridgen, L. N.; Mokhallalati, M. K.; Wu, M. J. J. Org. Chem. 1992, 57, 1237.
5. For recent examples of asymmetric synthesis of diarylmethylamines: (a) Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1996, 37, 4837. (b) Delorme, D.; Berthelette, C.; Lavoie, R.; Roberts, E. Tetrahedron Asym. 1998, 9, 3963. (c) Pridgen, L. N.; Mokhallalati, M. K.; Wu, M. J. J. Org. Chem. 1992, 57, 1237.
6. For recent examples of asymmetric synthesis of diarylmethylamines: (a) Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1996, 37, 4837. (b) Delorme, D.; Berthelette, C.; Lavoie, R.; Roberts, E. Tetrahedron Asym. 1998, 9, 3963. (c) Pridgen, L. N.; Mokhallalati, M. K.; Wu, M. J. J. Org. Chem. 1992, 57, 1237.
7. For a recent pertinent review on catalytic enantioselective addition to imines: Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
8. Catalytic asymmetric alkylation and allylation of imines and Mannich-type reaction have been reported. For recent examples: (a) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron Asym. 1995, 6, 2527. (b) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797. (c) Gittins née Jones, C. A.; North, M. Tetrahedron Asym. 1997, 8, 3789. Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (e) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242. (f) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153. (g) Fujiidera, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (h) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
9. Catalytic asymmetric alkylation and allylation of imines and Mannich-type reaction have been reported. For recent examples: (a) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron Asym. 1995, 6, 2527. (b) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797. (c) Gittins née Jones, C. A.; North, M. Tetrahedron Asym. 1997, 8, 3789. Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (e) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242. (f) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153. (g) Fujiidera, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (h) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
10. Catalytic asymmetric alkylation and allylation of imines and Mannich-type reaction have been reported. For recent examples: (a) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron Asym. 1995, 6, 2527. (b) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797. (c) Gittins née Jones, C. A.; North, M. Tetrahedron Asym. 1997, 8, 3789. Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (e) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242. (f) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153. (g) Fujiidera, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (h) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
11. Catalytic asymmetric alkylation and allylation of imines and Mannich-type reaction have been reported. For recent examples: (a) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron Asym. 1995, 6, 2527. (b) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797. (c) Gittins née Jones, C. A.; North, M. Tetrahedron Asym. 1997, 8, 3789. Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (e) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242. (f) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153. (g) Fujiidera, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (h) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
12. Catalytic asymmetric alkylation and allylation of imines and Mannich-type reaction have been reported. For recent examples: (a) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron Asym. 1995, 6, 2527. (b) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797. (c) Gittins née Jones, C. A.; North, M. Tetrahedron Asym. 1997, 8, 3789. Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (e) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242. (f) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153. (g) Fujiidera, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (h) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
13. Catalytic asymmetric alkylation and allylation of imines and Mannich-type reaction have been reported. For recent examples: (a) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron Asym. 1995, 6, 2527. (b) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797. (c) Gittins née Jones, C. A.; North, M. Tetrahedron Asym. 1997, 8, 3789. Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (e) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242. (f) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153. (g) Fujiidera, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (h) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
14. Catalytic asymmetric alkylation and allylation of imines and Mannich-type reaction have been reported. For recent examples: (a) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron Asym. 1995, 6, 2527. (b) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797. (c) Gittins née Jones, C. A.; North, M. Tetrahedron Asym. 1997, 8, 3789. Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (e) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242. (f) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153. (g) Fujiidera, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (h) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
15. Catalytic asymmetric alkylation and allylation of imines and Mannich-type reaction have been reported. For recent examples: (a) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron Asym. 1995, 6, 2527. (b) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797. (c) Gittins née Jones, C. A.; North, M. Tetrahedron Asym. 1997, 8, 3789. Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (e) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242. (f) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153. (g) Fujiidera, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (h) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
16. Catalytic asymmetric alkylation and allylation of imines and Mannich-type reaction have been reported. For recent examples: (a) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron Asym. 1995, 6, 2527. (b) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797. (c) Gittins née Jones, C. A.; North, M. Tetrahedron Asym. 1997, 8, 3789. Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (e) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242. (f) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153. (g) Fujiidera, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (h) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
17. (a) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887.
18. (b) Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945.
19. (c) Uozumi, Y.; Suzuki, N.; Ogiwara, A.; Hayashi, T. Tetrahedron 1994, 50, 4293.
20. Love, B. E.; Raje, P. S.; Williams, T. C., II Synlett 1994, 493.
21. The present arylation was found to proceed with high reproducibility on addition of LiF though the addition is not essential.
22. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.
23. Diarylmethylamines 8 undergo slow decomposition on exposure to the air or silica gel. Attempts to determine the enantiomeric purity of amines 8 themselves were not successful.
24. Takaya, H.; Mashima, S.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
25. Kagan, H. B.; Dang, T. P. J. Am. Chem. Soc. 1972, 94, 6429.
26. 20 +183 (c 1.00, chloroform).
27. 20 +10.8 (c 2.18, ethanol). (a) Clemo, G. R.; Gardner, C.; Raper, R. J. Chem. Soc. 1939, 1958.
28. (b) Opalka, C. J.; D'Ambra, T. E.; Faccone, J. J.; Bodson, G.; Cossement, E. Synthesis 1995, 766.
29. 20 +7.4 (c 0.5, chloroform).