Iridium-catalyzed asymmetric hydrosilylation of imines using chiral oxazolinyl-phosphine ligands

Organometallics

Volumn 18, Issue 11, 1999, Pages 2271-2274

  Takei, Izuru ^a   Nishibayashi, Yoshiaki ^a   Arikawa, Yasuyoshi ^b   Uemura, Sakae ^b   Hidai, Masanobu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000758920     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om981005w     Document Type: Article

References (35)

1. For reviews, see: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993. (b) Brunner, H.; Zettimeier, W. Handbook of Enantioselective Catalysis with Transition Metal Compounds; VCH: Weinheim, 1993. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994.
2. For reviews, see: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993. (b) Brunner, H.; Zettimeier, W. Handbook of Enantioselective Catalysis with Transition Metal Compounds; VCH: Weinheim, 1993. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994.
3. For reviews, see: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993. (b) Brunner, H.; Zettimeier, W. Handbook of Enantioselective Catalysis with Transition Metal Compounds; VCH: Weinheim, 1993. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994.
4. For recent examples of asymmetric hydrosilylation: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (b) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1994, 1375. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl 1994, 33, 111. (d) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503. (e) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Ohe, K.; Uemura, S. Organometallics 1996, 15, 370. (f) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597. (g) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. (h) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805. (i) Nishibayashi, Y.; Singh, J. D.; Arikawa, Y.; Uemura, S.; Hidai, M. J. Organomet. Chem. 1997, 531, 13. (j) Lee, S.; Lim, C. W.; Song, C. E.; Kim, I. O. Tetrahedron: Asymmetry 1997, 8, 4027. (k) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398.
5. For recent examples of asymmetric hydrosilylation: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (b) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1994, 1375. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl 1994, 33, 111. (d) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503. (e) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Ohe, K.; Uemura, S. Organometallics 1996, 15, 370. (f) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597. (g) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. (h) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805. (i) Nishibayashi, Y.; Singh, J. D.; Arikawa, Y.; Uemura, S.; Hidai, M. J. Organomet. Chem. 1997, 531, 13. (j) Lee, S.; Lim, C. W.; Song, C. E.; Kim, I. O. Tetrahedron: Asymmetry 1997, 8, 4027. (k) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398.
6. For recent examples of asymmetric hydrosilylation: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (b) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1994, 1375. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl 1994, 33, 111. (d) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503. (e) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Ohe, K.; Uemura, S. Organometallics 1996, 15, 370. (f) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597. (g) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. (h) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805. (i) Nishibayashi, Y.; Singh, J. D.; Arikawa, Y.; Uemura, S.; Hidai, M. J. Organomet. Chem. 1997, 531, 13. (j) Lee, S.; Lim, C. W.; Song, C. E.; Kim, I. O. Tetrahedron: Asymmetry 1997, 8, 4027. (k) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398.
7. For recent examples of asymmetric hydrosilylation: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (b) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1994, 1375. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl 1994, 33, 111. (d) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503. (e) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Ohe, K.; Uemura, S. Organometallics 1996, 15, 370. (f) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597. (g) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. (h) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805. (i) Nishibayashi, Y.; Singh, J. D.; Arikawa, Y.; Uemura, S.; Hidai, M. J. Organomet. Chem. 1997, 531, 13. (j) Lee, S.; Lim, C. W.; Song, C. E.; Kim, I. O. Tetrahedron: Asymmetry 1997, 8, 4027. (k) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398.
8. For recent examples of asymmetric hydrosilylation: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (b) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1994, 1375. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl 1994, 33, 111. (d) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503. (e) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Ohe, K.; Uemura, S. Organometallics 1996, 15, 370. (f) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597. (g) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. (h) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805. (i) Nishibayashi, Y.; Singh, J. D.; Arikawa, Y.; Uemura, S.; Hidai, M. J. Organomet. Chem. 1997, 531, 13. (j) Lee, S.; Lim, C. W.; Song, C. E.; Kim, I. O. Tetrahedron: Asymmetry 1997, 8, 4027. (k) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398.
9. For recent examples of asymmetric hydrosilylation: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (b) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1994, 1375. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl 1994, 33, 111. (d) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503. (e) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Ohe, K.; Uemura, S. Organometallics 1996, 15, 370. (f) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597. (g) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. (h) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805. (i) Nishibayashi, Y.; Singh, J. D.; Arikawa, Y.; Uemura, S.; Hidai, M. J. Organomet. Chem. 1997, 531, 13. (j) Lee, S.; Lim, C. W.; Song, C. E.; Kim, I. O. Tetrahedron: Asymmetry 1997, 8, 4027. (k) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398.
10. For recent examples of asymmetric hydrosilylation: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (b) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1994, 1375. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl 1994, 33, 111. (d) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503. (e) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Ohe, K.; Uemura, S. Organometallics 1996, 15, 370. (f) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597. (g) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. (h) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805. (i) Nishibayashi, Y.; Singh, J. D.; Arikawa, Y.; Uemura, S.; Hidai, M. J. Organomet. Chem. 1997, 531, 13. (j) Lee, S.; Lim, C. W.; Song, C. E.; Kim, I. O. Tetrahedron: Asymmetry 1997, 8, 4027. (k) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398.
11. For recent examples of asymmetric hydrosilylation: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (b) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1994, 1375. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl 1994, 33, 111. (d) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503. (e) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Ohe, K.; Uemura, S. Organometallics 1996, 15, 370. (f) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597. (g) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. (h) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805. (i) Nishibayashi, Y.; Singh, J. D.; Arikawa, Y.; Uemura, S.; Hidai, M. J. Organomet. Chem. 1997, 531, 13. (j) Lee, S.; Lim, C. W.; Song, C. E.; Kim, I. O. Tetrahedron: Asymmetry 1997, 8, 4027. (k) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398.
12. For recent examples of asymmetric hydrosilylation: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (b) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1994, 1375. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl 1994, 33, 111. (d) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503. (e) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Ohe, K.; Uemura, S. Organometallics 1996, 15, 370. (f) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597. (g) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. (h) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805. (i) Nishibayashi, Y.; Singh, J. D.; Arikawa, Y.; Uemura, S.; Hidai, M. J. Organomet. Chem. 1997, 531, 13. (j) Lee, S.; Lim, C. W.; Song, C. E.; Kim, I. O. Tetrahedron: Asymmetry 1997, 8, 4027. (k) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398.
13. For recent examples of asymmetric hydrosilylation: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (b) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1994, 1375. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl 1994, 33, 111. (d) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503. (e) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Ohe, K.; Uemura, S. Organometallics 1996, 15, 370. (f) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597. (g) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. (h) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805. (i) Nishibayashi, Y.; Singh, J. D.; Arikawa, Y.; Uemura, S.; Hidai, M. J. Organomet. Chem. 1997, 531, 13. (j) Lee, S.; Lim, C. W.; Song, C. E.; Kim, I. O. Tetrahedron: Asymmetry 1997, 8, 4027. (k) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398.
14. For recent examples of asymmetric hydrosilylation: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (b) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1994, 1375. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl 1994, 33, 111. (d) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503. (e) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Ohe, K.; Uemura, S. Organometallics 1996, 15, 370. (f) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597. (g) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. (h) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805. (i) Nishibayashi, Y.; Singh, J. D.; Arikawa, Y.; Uemura, S.; Hidai, M. J. Organomet. Chem. 1997, 531, 13. (j) Lee, S.; Lim, C. W.; Song, C. E.; Kim, I. O. Tetrahedron: Asymmetry 1997, 8, 4027. (k) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398.
15. Recent examples of asymmetric hydrogenation of imines: (a) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (b) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703. (c) Tani, K.; Onouchi, J.; Yamagata, T.; Kataoka, Y. Chem. Lett. 1995, 955. (d) Schnider, P.; Koch, G.; Pretot, R.; Wang, G.; Bohnen, F. R.; Krüger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887. (e) Zhu, G.; Zhang, X. Tetrahedron: Asymmetry 1998, 9, 2415. (f) Satoh, K.; Inenaga, M.; Kanai, K. Tetrahedron: Asymmetry 1998, 9, 2657. (g) Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry 1998, 9, 183.
16. Recent examples of asymmetric hydrogenation of imines: (a) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (b) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703. (c) Tani, K.; Onouchi, J.; Yamagata, T.; Kataoka, Y. Chem. Lett. 1995, 955. (d) Schnider, P.; Koch, G.; Pretot, R.; Wang, G.; Bohnen, F. R.; Krüger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887. (e) Zhu, G.; Zhang, X. Tetrahedron: Asymmetry 1998, 9, 2415. (f) Satoh, K.; Inenaga, M.; Kanai, K. Tetrahedron: Asymmetry 1998, 9, 2657. (g) Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry 1998, 9, 183.
17. Recent examples of asymmetric hydrogenation of imines: (a) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (b) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703. (c) Tani, K.; Onouchi, J.; Yamagata, T.; Kataoka, Y. Chem. Lett. 1995, 955. (d) Schnider, P.; Koch, G.; Pretot, R.; Wang, G.; Bohnen, F. R.; Krüger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887. (e) Zhu, G.; Zhang, X. Tetrahedron: Asymmetry 1998, 9, 2415. (f) Satoh, K.; Inenaga, M.; Kanai, K. Tetrahedron: Asymmetry 1998, 9, 2657. (g) Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry 1998, 9, 183.
18. Recent examples of asymmetric hydrogenation of imines: (a) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (b) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703. (c) Tani, K.; Onouchi, J.; Yamagata, T.; Kataoka, Y. Chem. Lett. 1995, 955. (d) Schnider, P.; Koch, G.; Pretot, R.; Wang, G.; Bohnen, F. R.; Krüger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887. (e) Zhu, G.; Zhang, X. Tetrahedron: Asymmetry 1998, 9, 2415. (f) Satoh, K.; Inenaga, M.; Kanai, K. Tetrahedron: Asymmetry 1998, 9, 2657. (g) Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry 1998, 9, 183.
19. Recent examples of asymmetric hydrogenation of imines: (a) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (b) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703. (c) Tani, K.; Onouchi, J.; Yamagata, T.; Kataoka, Y. Chem. Lett. 1995, 955. (d) Schnider, P.; Koch, G.; Pretot, R.; Wang, G.; Bohnen, F. R.; Krüger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887. (e) Zhu, G.; Zhang, X. Tetrahedron: Asymmetry 1998, 9, 2415. (f) Satoh, K.; Inenaga, M.; Kanai, K. Tetrahedron: Asymmetry 1998, 9, 2657. (g) Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry 1998, 9, 183.
20. Recent examples of asymmetric hydrogenation of imines: (a) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (b) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703. (c) Tani, K.; Onouchi, J.; Yamagata, T.; Kataoka, Y. Chem. Lett. 1995, 955. (d) Schnider, P.; Koch, G.; Pretot, R.; Wang, G.; Bohnen, F. R.; Krüger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887. (e) Zhu, G.; Zhang, X. Tetrahedron: Asymmetry 1998, 9, 2415. (f) Satoh, K.; Inenaga, M.; Kanai, K. Tetrahedron: Asymmetry 1998, 9, 2657. (g) Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry 1998, 9, 183.
21. Recent examples of asymmetric hydrogenation of imines: (a) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (b) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703. (c) Tani, K.; Onouchi, J.; Yamagata, T.; Kataoka, Y. Chem. Lett. 1995, 955. (d) Schnider, P.; Koch, G.; Pretot, R.; Wang, G.; Bohnen, F. R.; Krüger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887. (e) Zhu, G.; Zhang, X. Tetrahedron: Asymmetry 1998, 9, 2415. (f) Satoh, K.; Inenaga, M.; Kanai, K. Tetrahedron: Asymmetry 1998, 9, 2657. (g) Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry 1998, 9, 183.
22. Asymmetric transfer hydrogenation of imines: Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916-4917.
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