Carbohydrate Phosphinites as Practical Ligands in Asymmetric Catalysis: Electronic Effects and Dependence of Backbone Chirality in Rh-Catalyzed Asymmetric Hydrogenations. Synthesis of R- or S-Amino Acids Using Natural Sugars as Ligand Precursors

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 6012-6025

  RajanBabu, T V ^a   Ayers, Timothy A ^a   Halliday, Gary A ^a   You, Kimberly K ^a   Calabrese, Joseph C ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001486820     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970884d     Document Type: Article

References (129)

1. For recent monographs and reviews see: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994. (b) Ojima, I. Asymmetric Synthesis; Verlag: New York, 1993. (c) Collins, A. N.; Sheldrake, G. N.; Crosby, J. Chirality in Industry; John Wiley: New York, 1992. (d) Bosnich, B. Asymmetric Catalysis; Martinus Nijhoff Publishers: Dordrecht, 1986. (e) Brunner, H. Synthesis 1988, 645. ff) Brown, J. M.; Davies, S. G. Nature 1989, 342, 631. (h) Pfaltz, A. Chimia 1990, 44, 202. (i) Nugent, W. A.; RajanBabu, T. V.; Burk, M. J. Science 1993, 259, 479.
2. For recent monographs and reviews see: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994. (b) Ojima, I. Asymmetric Synthesis; Verlag: New York, 1993. (c) Collins, A. N.; Sheldrake, G. N.; Crosby, J. Chirality in Industry; John Wiley: New York, 1992. (d) Bosnich, B. Asymmetric Catalysis; Martinus Nijhoff Publishers: Dordrecht, 1986. (e) Brunner, H. Synthesis 1988, 645. ff) Brown, J. M.; Davies, S. G. Nature 1989, 342, 631. (h) Pfaltz, A. Chimia 1990, 44, 202. (i) Nugent, W. A.; RajanBabu, T. V.; Burk, M. J. Science 1993, 259, 479.
3. For recent monographs and reviews see: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994. (b) Ojima, I. Asymmetric Synthesis; Verlag: New York, 1993. (c) Collins, A. N.; Sheldrake, G. N.; Crosby, J. Chirality in Industry; John Wiley: New York, 1992. (d) Bosnich, B. Asymmetric Catalysis; Martinus Nijhoff Publishers: Dordrecht, 1986. (e) Brunner, H. Synthesis 1988, 645. ff) Brown, J. M.; Davies, S. G. Nature 1989, 342, 631. (h) Pfaltz, A. Chimia 1990, 44, 202. (i) Nugent, W. A.; RajanBabu, T. V.; Burk, M. J. Science 1993, 259, 479.
4. For recent monographs and reviews see: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994. (b) Ojima, I. Asymmetric Synthesis; Verlag: New York, 1993. (c) Collins, A. N.; Sheldrake, G. N.; Crosby, J. Chirality in Industry; John Wiley: New York, 1992. (d) Bosnich, B. Asymmetric Catalysis; Martinus Nijhoff Publishers: Dordrecht, 1986. (e) Brunner, H. Synthesis 1988, 645. ff) Brown, J. M.; Davies, S. G. Nature 1989, 342, 631. (h) Pfaltz, A. Chimia 1990, 44, 202. (i) Nugent, W. A.; RajanBabu, T. V.; Burk, M. J. Science 1993, 259, 479.
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6. For recent monographs and reviews see: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994. (b) Ojima, I. Asymmetric Synthesis; Verlag: New York, 1993. (c) Collins, A. N.; Sheldrake, G. N.; Crosby, J. Chirality in Industry; John Wiley: New York, 1992. (d) Bosnich, B. Asymmetric Catalysis; Martinus Nijhoff Publishers: Dordrecht, 1986. (e) Brunner, H. Synthesis 1988, 645. ff) Brown, J. M.; Davies, S. G. Nature 1989, 342, 631. (h) Pfaltz, A. Chimia 1990, 44, 202. (i) Nugent, W. A.; RajanBabu, T. V.; Burk, M. J. Science 1993, 259, 479.
7. For recent monographs and reviews see: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994. (b) Ojima, I. Asymmetric Synthesis; Verlag: New York, 1993. (c) Collins, A. N.; Sheldrake, G. N.; Crosby, J. Chirality in Industry; John Wiley: New York, 1992. (d) Bosnich, B. Asymmetric Catalysis; Martinus Nijhoff Publishers: Dordrecht, 1986. (e) Brunner, H. Synthesis 1988, 645. ff) Brown, J. M.; Davies, S. G. Nature 1989, 342, 631. (h) Pfaltz, A. Chimia 1990, 44, 202. (i) Nugent, W. A.; RajanBabu, T. V.; Burk, M. J. Science 1993, 259, 479.
8. For recent monographs and reviews see: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994. (b) Ojima, I. Asymmetric Synthesis; Verlag: New York, 1993. (c) Collins, A. N.; Sheldrake, G. N.; Crosby, J. Chirality in Industry; John Wiley: New York, 1992. (d) Bosnich, B. Asymmetric Catalysis; Martinus Nijhoff Publishers: Dordrecht, 1986. (e) Brunner, H. Synthesis 1988, 645. ff) Brown, J. M.; Davies, S. G. Nature 1989, 342, 631. (h) Pfaltz, A. Chimia 1990, 44, 202. (i) Nugent, W. A.; RajanBabu, T. V.; Burk, M. J. Science 1993, 259, 479.
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25. See for example: (a) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703. (b) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. (c) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. (d) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (e) Togni, A.; Breutel, C.; Schnyder, A.; Spidler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (f) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (g) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. (h) Rieck, H.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2687.
26. See for example: (a) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703. (b) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. (c) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. (d) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (e) Togni, A.; Breutel, C.; Schnyder, A.; Spidler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (f) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (g) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. (h) Rieck, H.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2687.
27. See for example: (a) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703. (b) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. (c) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. (d) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (e) Togni, A.; Breutel, C.; Schnyder, A.; Spidler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (f) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (g) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. (h) Rieck, H.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2687.
28. See for example: (a) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703. (b) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. (c) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. (d) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (e) Togni, A.; Breutel, C.; Schnyder, A.; Spidler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (f) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (g) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. (h) Rieck, H.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2687.
29. See for example: (a) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703. (b) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. (c) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. (d) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (e) Togni, A.; Breutel, C.; Schnyder, A.; Spidler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (f) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (g) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. (h) Rieck, H.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2687.
30. See for example: (a) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703. (b) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. (c) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. (d) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (e) Togni, A.; Breutel, C.; Schnyder, A.; Spidler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (f) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (g) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. (h) Rieck, H.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2687.
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43. The use of carbohydrate phosphinites for hydrogenation of dehydroamino acids have been known since 1978: (a) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 19, 1635. (b) Selke, R. React. Kinet. Catal. Lett. 1979, 10, 135. (c) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (d) For the most recent contributions from the Selke group see: Berens, U.; Selke, R. Tetrahedron: Asymmetry 1996, 7, 2055.
44. The use of carbohydrate phosphinites for hydrogenation of dehydroamino acids have been known since 1978: (a) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 19, 1635. (b) Selke, R. React. Kinet. Catal. Lett. 1979, 10, 135. (c) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (d) For the most recent contributions from the Selke group see: Berens, U.; Selke, R. Tetrahedron: Asymmetry 1996, 7, 2055.
45. The use of carbohydrate phosphinites for hydrogenation of dehydroamino acids have been known since 1978: (a) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 19, 1635. (b) Selke, R. React. Kinet. Catal. Lett. 1979, 10, 135. (c) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (d) For the most recent contributions from the Selke group see: Berens, U.; Selke, R. Tetrahedron: Asymmetry 1996, 7, 2055.
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51. Anecdotal evidence of electronic effects in Rh-catalyzed hydrogenation dates back to some of the original studies done by Kagan. See for example: (a) Dang, T. P.; Poulin, J. C.; Kagan, H. B. J. Organomet. Chem. 1975, 91, 105. (b) Hengartner, U.; Valentine, D., Jr.; Johnson, K. K.; Larscheid, M. E.; Pigott, F.; Scheidl, F.; Scott, J. W.; Sun, R. C.; Townsend, J. M.; Williams, T. H. J. Org. Chem. 1979, 44, 3741. (c) Yamagishi, T.; Yatagai, M.; Hatakeyama, H.; Hida, M. Bull. Chem. Soc. Jpn. 1984, 57, 1897. (d) Inoguchi, K.; Morimoto, T.; Achiwa, K. J. Organomet. Chem. 1989, 370, C9. (e) Werz, U.; Brune, H. A. J. Organomet. Chem. 1989, 365, 367. (f) Morimoto, T.; Chiba, M.; Achiwa, K. Chem. Pharm. Bull. 1992, 40, 2894.
52. Anecdotal evidence of electronic effects in Rh-catalyzed hydrogenation dates back to some of the original studies done by Kagan. See for example: (a) Dang, T. P.; Poulin, J. C.; Kagan, H. B. J. Organomet. Chem. 1975, 91, 105. (b) Hengartner, U.; Valentine, D., Jr.; Johnson, K. K.; Larscheid, M. E.; Pigott, F.; Scheidl, F.; Scott, J. W.; Sun, R. C.; Townsend, J. M.; Williams, T. H. J. Org. Chem. 1979, 44, 3741. (c) Yamagishi, T.; Yatagai, M.; Hatakeyama, H.; Hida, M. Bull. Chem. Soc. Jpn. 1984, 57, 1897. (d) Inoguchi, K.; Morimoto, T.; Achiwa, K. J. Organomet. Chem. 1989, 370, C9. (e) Werz, U.; Brune, H. A. J. Organomet. Chem. 1989, 365, 367. (f) Morimoto, T.; Chiba, M.; Achiwa, K. Chem. Pharm. Bull. 1992, 40, 2894.
53. Anecdotal evidence of electronic effects in Rh-catalyzed hydrogenation dates back to some of the original studies done by Kagan. See for example: (a) Dang, T. P.; Poulin, J. C.; Kagan, H. B. J. Organomet. Chem. 1975, 91, 105. (b) Hengartner, U.; Valentine, D., Jr.; Johnson, K. K.; Larscheid, M. E.; Pigott, F.; Scheidl, F.; Scott, J. W.; Sun, R. C.; Townsend, J. M.; Williams, T. H. J. Org. Chem. 1979, 44, 3741. (c) Yamagishi, T.; Yatagai, M.; Hatakeyama, H.; Hida, M. Bull. Chem. Soc. Jpn. 1984, 57, 1897. (d) Inoguchi, K.; Morimoto, T.; Achiwa, K. J. Organomet. Chem. 1989, 370, C9. (e) Werz, U.; Brune, H. A. J. Organomet. Chem. 1989, 365, 367. (f) Morimoto, T.; Chiba, M.; Achiwa, K. Chem. Pharm. Bull. 1992, 40, 2894.
54. Anecdotal evidence of electronic effects in Rh-catalyzed hydrogenation dates back to some of the original studies done by Kagan. See for example: (a) Dang, T. P.; Poulin, J. C.; Kagan, H. B. J. Organomet. Chem. 1975, 91, 105. (b) Hengartner, U.; Valentine, D., Jr.; Johnson, K. K.; Larscheid, M. E.; Pigott, F.; Scheidl, F.; Scott, J. W.; Sun, R. C.; Townsend, J. M.; Williams, T. H. J. Org. Chem. 1979, 44, 3741. (c) Yamagishi, T.; Yatagai, M.; Hatakeyama, H.; Hida, M. Bull. Chem. Soc. Jpn. 1984, 57, 1897. (d) Inoguchi, K.; Morimoto, T.; Achiwa, K. J. Organomet. Chem. 1989, 370, C9. (e) Werz, U.; Brune, H. A. J. Organomet. Chem. 1989, 365, 367. (f) Morimoto, T.; Chiba, M.; Achiwa, K. Chem. Pharm. Bull. 1992, 40, 2894.
55. Anecdotal evidence of electronic effects in Rh-catalyzed hydrogenation dates back to some of the original studies done by Kagan. See for example: (a) Dang, T. P.; Poulin, J. C.; Kagan, H. B. J. Organomet. Chem. 1975, 91, 105. (b) Hengartner, U.; Valentine, D., Jr.; Johnson, K. K.; Larscheid, M. E.; Pigott, F.; Scheidl, F.; Scott, J. W.; Sun, R. C.; Townsend, J. M.; Williams, T. H. J. Org. Chem. 1979, 44, 3741. (c) Yamagishi, T.; Yatagai, M.; Hatakeyama, H.; Hida, M. Bull. Chem. Soc. Jpn. 1984, 57, 1897. (d) Inoguchi, K.; Morimoto, T.; Achiwa, K. J. Organomet. Chem. 1989, 370, C9. (e) Werz, U.; Brune, H. A. J. Organomet. Chem. 1989, 365, 367. (f) Morimoto, T.; Chiba, M.; Achiwa, K. Chem. Pharm. Bull. 1992, 40, 2894.
56. Anecdotal evidence of electronic effects in Rh-catalyzed hydrogenation dates back to some of the original studies done by Kagan. See for example: (a) Dang, T. P.; Poulin, J. C.; Kagan, H. B. J. Organomet. Chem. 1975, 91, 105. (b) Hengartner, U.; Valentine, D., Jr.; Johnson, K. K.; Larscheid, M. E.; Pigott, F.; Scheidl, F.; Scott, J. W.; Sun, R. C.; Townsend, J. M.; Williams, T. H. J. Org. Chem. 1979, 44, 3741. (c) Yamagishi, T.; Yatagai, M.; Hatakeyama, H.; Hida, M. Bull. Chem. Soc. Jpn. 1984, 57, 1897. (d) Inoguchi, K.; Morimoto, T.; Achiwa, K. J. Organomet. Chem. 1989, 370, C9. (e) Werz, U.; Brune, H. A. J. Organomet. Chem. 1989, 365, 367. (f) Morimoto, T.; Chiba, M.; Achiwa, K. Chem. Pharm. Bull. 1992, 40, 2894.
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