Methylene-bridged P-chiral diphosphines in highly enantioselective reactions

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 2988-2989

  Yamanoi, Yoshinori ^a   Imamoto, Tsuneo ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; PHOSPHINE DERIVATIVE;

ARTICLE; BINDING AFFINITY; CATALYSIS; CHIRALITY; CRYSTALLIZATION; HYDROXYLATION; LIGAND BINDING; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033617302     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990131m     Document Type: Article

References (34)

1. For representative reviews, see the following: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994. (b) Ojima, I., Ed. Catalytic Asymmetric Synthesis; VCH Publishers: Weinheim, 1993.
2. For representative reviews, see the following: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994. (b) Ojima, I., Ed. Catalytic Asymmetric Synthesis; VCH Publishers: Weinheim, 1993.
3. For recently reported representative chiral diphosphines, see: (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207. (b) RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. (c) Zhang, F. Y.; Pai, C. C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808. (d) Qiao, S.; Fu, G. C. J. Org. Chem. 1998, 63, 4168. (e) Jiang, Q.; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. Engl. 1998, 37, 1100.
4. For recently reported representative chiral diphosphines, see: (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207. (b) RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. (c) Zhang, F. Y.; Pai, C. C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808. (d) Qiao, S.; Fu, G. C. J. Org. Chem. 1998, 63, 4168. (e) Jiang, Q.; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. Engl. 1998, 37, 1100.
5. For recently reported representative chiral diphosphines, see: (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207. (b) RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. (c) Zhang, F. Y.; Pai, C. C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808. (d) Qiao, S.; Fu, G. C. J. Org. Chem. 1998, 63, 4168. (e) Jiang, Q.; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. Engl. 1998, 37, 1100.
6. For recently reported representative chiral diphosphines, see: (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207. (b) RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. (c) Zhang, F. Y.; Pai, C. C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808. Qiao, S.; Fu, G. C. J. Org. Chem. 1998, 63, 4168. (e) Jiang, Q.; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. Engl. 1998, 37, 1100.
7. For recently reported representative chiral diphosphines, see: (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207. (b) RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. (c) Zhang, F. Y.; Pai, C. C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808. (d) Qiao, S.; Fu, G. C. J. Org. Chem. 1998, 63, 4168. (e) Jiang, Q.; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. Engl. 1998, 37, 1100.
8. We abbreviate these chiral ligands as MiniPHOS, because they are quite small when compared with all the chiral diphosphines reported so far.
9. A few chiral 1,1-diphosphines have been described in the literature, and there has been only one report dealing with Rh-catalyzed asymmetric hydrogenations with very low enantioselectivity. (a) Marinetti, A.; Menn, C. L.; Ricard, L. Organometallics 1995, 14, 4983. (b) Babu, R. P. K.; Krishnamurthy, S. S.; Nethaji, M. Tetrahedron: Asymmetry 1995, 6, 427. Brunner, H.; Furst, J. Tetrahedron 1994, 50, 4303.
10. A few chiral 1,1-diphosphines have been described in the literature, and there has been only one report dealing with Rh-catalyzed asymmetric hydrogenations with very low enantioselectivity. (a) Marinetti, A.; Menn, C. L.; Ricard, L. Organometallics 1995, 14, 4983. (b) Babu, R. P. K.; Krishnamurthy, S. S.; Nethaji, M. Tetrahedron: Asymmetry 1995, 6, 427. Brunner, H.; Furst, J. Tetrahedron 1994, 50, 4303.
11. A few chiral 1,1-diphosphines have been described in the literature, and there has been only one report dealing with Rh-catalyzed asymmetric hydrogenations with very low enantioselectivity. (a) Marinetti, A.; Menn, C. L.; Ricard, L. Organometallics 1995, 14, 4983. (b) Babu, R. P. K.; Krishnamurthy, S. S.; Nethaji, M. Tetrahedron: Asymmetry 1995, 6, 427. Brunner, H.; Furst, J. Tetrahedron 1994, 50, 4303.
12. (a) Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244.
13. (b) Jugé, S.; Stephane, M.; Laffitte, J. A.; Genêt, J. P. Tetrahedron Lett. 1990, 31, 6357.
14. Ohff, M.; Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1998, 1391.
15. Carboni, B.; Monnier, L. Tetrahedron 1999, 55, 1197 and references cited therein.
16. Enantioselective deprotonation of aryl- or alkyldimethylphosphineboranes with (-)-sparteine/s-BuLi complex was reported. (a) Muci, A. R.; Campos, K. R.; Evans, D. A J. Am. Chem. Soc. 1995, 117, 9075. (b) Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635.
17. Enantioselective deprotonation of aryl- or alkyldimethylphosphineboranes with (-)-sparteine/s-BuLi complex was reported. (a) Muci, A. R.; Campos, K. R.; Evans, D. A J. Am. Chem. Soc. 1995, 117, 9075. (b) Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635.
18. McKinstry, L.; Livinghouse, T. Tetrahedron Lett. 1994, 35, 9319.
19. 3; temperature of data collection 293 K; 1619 unique reflections (I > 2.0σ(I)); R = 0.067; Rw = 0.089; GOF = 1.41.
20. Knowles, W. S. Acc. Chem. Res. 1983, 16, 106.
21. Burk et al. have demonstrated that Rh and Ru catalysts bearing DuPHOS or BPE exhibit very high enantioselectivities in various asymmetric hydrogenations. (a) Burk, M. J.; Gross, M. F.; Harper, T. G. P.; Kalberg, C. S.; Lee, J. R.; Martinez, J. P. Pure Appl. Chem. 1996, 68, 37. (b) Burk, M. J.; Wang, Y. M.; Lee, J. R. J. Am. Chem. Soc. 1996, 118, 5142. Burk, M. J.; Kalberg, C. S.; Pizzano, A. J. Am. Chem. Soc. 1998, 120, 4345. Burk, M. J.; Bienewald, F.; Harris, M.; Zanotti-Gerosa, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 1931.
22. Burk et al. have demonstrated that Rh and Ru catalysts bearing DuPHOS or BPE exhibit very high enantioselectivities in various asymmetric hydrogenations. (a) Burk, M. J.; Gross, M. F.; Harper, T. G. P.; Kalberg, C. S.; Lee, J. R.; Martinez, J. P. Pure Appl. Chem. 1996, 68, 37. (b) Burk, M. J.; Wang, Y. M.; Lee, J. R. J. Am. Chem. Soc. 1996, 118, 5142. Burk, M. J.; Kalberg, C. S.; Pizzano, A. J. Am. Chem. Soc. 1998, 120, 4345. Burk, M. J.; Bienewald, F.; Harris, M.; Zanotti-Gerosa, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 1931.
23. Burk et al. have demonstrated that Rh and Ru catalysts bearing DuPHOS or BPE exhibit very high enantioselectivities in various asymmetric hydrogenations. (a) Burk, M. J.; Gross, M. F.; Harper, T. G. P.; Kalberg, C. S.; Lee, J. R.; Martinez, J. P. Pure Appl. Chem. 1996, 68, 37. (b) Burk, M. J.; Wang, Y. M.; Lee, J. R. J. Am. Chem. Soc. 1996, 118, 5142. Burk, M. J.; Kalberg, C. S.; Pizzano, A. J. Am. Chem. Soc. 1998, 120, 4345. Burk, M. J.; Bienewald, F.; Harris, M.; Zanotti-Gerosa, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 1931.
24. Burk et al. have demonstrated that Rh and Ru catalysts bearing DuPHOS or BPE exhibit very high enantioselectivities in various asymmetric hydrogenations. (a) Burk, M. J.; Gross, M. F.; Harper, T. G. P.; Kalberg, C. S.; Lee, J. R.; Martinez, J. P. Pure Appl. Chem. 1996, 68, 37. (b) Burk, M. J.; Wang, Y. M.; Lee, J. R. J. Am. Chem. Soc. 1996, 118, 5142. Burk, M. J.; Kalberg, C. S.; Pizzano, A. J. Am. Chem. Soc. 1998, 120, 4345. Burk, M. J.; Bienewald, F.; Harris, M.; Zanotti-Gerosa, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 1931.
25. Hoerrner et al. reported asymmetric hydrogenation of β,β-disubstituted dehydroamino acid derivatives to prepare β-methyltryptophan with excellent enantiomeric excess. Hoerrner, R. S.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 3455.
26. 13
27. Sawamura, M.; Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9602.
28. 11-MiniPHOS >99.9%; i-Pr-MiniPHOS 98%) were observed in this reaction.
29. It is reasonable to consider that under the reaction conditions the bischelate rhodium complexes dissociate to the free diphosphines and the monochelate complexes which act as the actual catalyst species.
30. Kuwano, R.; Uemura, T.; Saitoh, M.; Ito, Y. Tetrahedron Lett. 1999, 40, 1327 and references cited therein.
31. (a) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
32. (b) Krause, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 283.
33. (a) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620.
34. (b) Knöbel, A. K. H.; Escher, I. H.; Pfaltz, A. Synlett 1997, 1429.