Catalytic asymmetric synthesis of α-hydroxy phosphonates using the Al-Li-BINOL complex

Journal of Organic Chemistry

Volumn 61, Issue 9, 1996, Pages 2926-2927

  Arai, Takayoshi ^a   Bougauchi, Masahiro ^a   Sasai, Hiroaki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029981019     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960180o     Document Type: Article

References (35)

1. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5587-5590. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5591-5594. Sikorski, J. A.; Miller, M. J.; Braccolino, D. S.; Cleary, D. G.; Corey, S. D.; Font, J. L.; Gruys, K. J.; Han C. Y.; Lin, K. C.; Pansegrau, P. D.; Ream, J. E.; Schnur, D.; Shah, A.; Walker, M. C. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 76, 375-378. Paterson, M. L.; Corey, S. D.; Sikorski, J. A.; Walker, M. C. Abstracts of Papers, 203rd American Chemical Society National Meeting, San Francisco, 1992, ORGN 469. Stowasser, B.; Budt, K-H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625-6628. Moore, M. L.; Dreyer, G. B. Prespect. Drug Discovery Des. 1993, 1, 85-108.
2. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5587-5590. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5591-5594. Sikorski, J. A.; Miller, M. J.; Braccolino, D. S.; Cleary, D. G.; Corey, S. D.; Font, J. L.; Gruys, K. J.; Han C. Y.; Lin, K. C.; Pansegrau, P. D.; Ream, J. E.; Schnur, D.; Shah, A.; Walker, M. C. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 76, 375-378. Paterson, M. L.; Corey, S. D.; Sikorski, J. A.; Walker, M. C. Abstracts of Papers, 203rd American Chemical Society National Meeting, San Francisco, 1992, ORGN 469. Stowasser, B.; Budt, K-H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625-6628. Moore, M. L.; Dreyer, G. B. Prespect. Drug Discovery Des. 1993, 1, 85-108.
3. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5587-5590. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5591-5594. Sikorski, J. A.; Miller, M. J.; Braccolino, D. S.; Cleary, D. G.; Corey, S. D.; Font, J. L.; Gruys, K. J.; Han C. Y.; Lin, K. C.; Pansegrau, P. D.; Ream, J. E.; Schnur, D.; Shah, A.; Walker, M. C. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 76, 375-378. Paterson, M. L.; Corey, S. D.; Sikorski, J. A.; Walker, M. C. Abstracts of Papers, 203rd American Chemical Society National Meeting, San Francisco, 1992, ORGN 469. Stowasser, B.; Budt, K-H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625-6628. Moore, M. L.; Dreyer, G. B. Prespect. Drug Discovery Des. 1993, 1, 85-108.
4. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5587-5590. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5591-5594. Sikorski, J. A.; Miller, M. J.; Braccolino, D. S.; Cleary, D. G.; Corey, S. D.; Font, J. L.; Gruys, K. J.; Han C. Y.; Lin, K. C.; Pansegrau, P. D.; Ream, J. E.; Schnur, D.; Shah, A.; Walker, M. C. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 76, 375-378. Paterson, M. L.; Corey, S. D.; Sikorski, J. A.; Walker, M. C. Abstracts of Papers, 203rd American Chemical Society National Meeting, San Francisco, 1992, ORGN 469. Stowasser, B.; Budt, K-H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625-6628. Moore, M. L.; Dreyer, G. B. Prespect. Drug Discovery Des. 1993, 1, 85-108.
5. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5587-5590. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5591-5594. Sikorski, J. A.; Miller, M. J.; Braccolino, D. S.; Cleary, D. G.; Corey, S. D.; Font, J. L.; Gruys, K. J.; Han C. Y.; Lin, K. C.; Pansegrau, P. D.; Ream, J. E.; Schnur, D.; Shah, A.; Walker, M. C. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 76, 375-378. Paterson, M. L.; Corey, S. D.; Sikorski, J. A.; Walker, M. C. Abstracts of Papers, 203rd American Chemical Society National Meeting, San Francisco, 1992, ORGN 469. Stowasser, B.; Budt, K-H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625-6628. Moore, M. L.; Dreyer, G. B. Prespect. Drug Discovery Des. 1993, 1, 85-108.
6. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5587-5590. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5591-5594. Sikorski, J. A.; Miller, M. J.; Braccolino, D. S.; Cleary, D. G.; Corey, S. D.; Font, J. L.; Gruys, K. J.; Han C. Y.; Lin, K. C.; Pansegrau, P. D.; Ream, J. E.; Schnur, D.; Shah, A.; Walker, M. C. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 76, 375-378. Paterson, M. L.; Corey, S. D.; Sikorski, J. A.; Walker, M. C. Abstracts of Papers, 203rd American Chemical Society National Meeting, San Francisco, 1992, ORGN 469. Stowasser, B.; Budt, K-H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625-6628. Moore, M. L.; Dreyer, G. B. Prespect. Drug Discovery Des. 1993, 1, 85-108.
7. Hammerschmidt, F.; Völlenkle, H. Liebigs Ann. Chem. 1989, 577-583. Yokomatsu, T.; Shibuya, S. Tetrahedron: Asymm. 1992, 3, 377-378. Baraldi, P. G.; Guarneri, M.; Moroder, F.; Pollini, G. P.; Simoni, D. Synthesis 1982, 653-654. Maier, L. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 76, 379-382.
8. Hammerschmidt, F.; Völlenkle, H. Liebigs Ann. Chem. 1989, 577-583. Yokomatsu, T.; Shibuya, S. Tetrahedron: Asymm. 1992, 3, 377-378. Baraldi, P. G.; Guarneri, M.; Moroder, F.; Pollini, G. P.; Simoni, D. Synthesis 1982, 653-654. Maier, L. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 76, 379-382.
9. Hammerschmidt, F.; Völlenkle, H. Liebigs Ann. Chem. 1989, 577-583. Yokomatsu, T.; Shibuya, S. Tetrahedron: Asymm. 1992, 3, 377-378. Baraldi, P. G.; Guarneri, M.; Moroder, F.; Pollini, G. P.; Simoni, D. Synthesis 1982, 653-654. Maier, L. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 76, 379-382.
10. Hammerschmidt, F.; Völlenkle, H. Liebigs Ann. Chem. 1989, 577-583. Yokomatsu, T.; Shibuya, S. Tetrahedron: Asymm. 1992, 3, 377-378. Baraldi, P. G.; Guarneri, M.; Moroder, F.; Pollini, G. P.; Simoni, D. Synthesis 1982, 653-654. Maier, L. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 76, 379-382.
11. Öhler, E.; Kotzinger, S. Synthesis 1993, 497-502 and references cited therein. For a review see: Kafarski, P; Lejczak, B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63, 193-215.
12. Öhler, E.; Kotzinger, S. Synthesis 1993, 497-502 and references cited therein. For a review see: Kafarski, P; Lejczak, B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63, 193-215.
13. Kametani, T.; Kigasawa, K.; Hiiragi, M.; Wakisaka, K.; Haga, S.; Sugi, H.; Tanigawa, K.; Suzuki, Y.; Fukawa, K.; Irino, O.; Saita, O.; Yamabe, S.; Heterocycles 1981, 16, 1205-1242. Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Lambert, R. W.; Lloyd, W. J.; Ringrose, P. S. Antimicrob. Agents Chemother. 1979, 15, 696-705. Allen, J. G.; Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Holmes, S. W.; Lambert, R. W.; Nisbet, L. J.; Ringrose, P. S. Antimicrob. Agents Chemother. 1979, 15, 684-695.
14. Kametani, T.; Kigasawa, K.; Hiiragi, M.; Wakisaka, K.; Haga, S.; Sugi, H.; Tanigawa, K.; Suzuki, Y.; Fukawa, K.; Irino, O.; Saita, O.; Yamabe, S.; Heterocycles 1981, 16, 1205-1242. Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Lambert, R. W.; Lloyd, W. J.; Ringrose, P. S. Antimicrob. Agents Chemother. 1979, 15, 696-705. Allen, J. G.; Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Holmes, S. W.; Lambert, R. W.; Nisbet, L. J.; Ringrose, P. S. Antimicrob. Agents Chemother. 1979, 15, 684-695.
15. Kametani, T.; Kigasawa, K.; Hiiragi, M.; Wakisaka, K.; Haga, S.; Sugi, H.; Tanigawa, K.; Suzuki, Y.; Fukawa, K.; Irino, O.; Saita, O.; Yamabe, S.; Heterocycles 1981, 16, 1205-1242. Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Lambert, R. W.; Lloyd, W. J.; Ringrose, P. S. Antimicrob. Agents Chemother. 1979, 15, 696-705. Allen, J. G.; Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Holmes, S. W.; Lambert, R. W.; Nisbet, L. J.; Ringrose, P. S. Antimicrob. Agents Chemother. 1979, 15, 684-695.
16. Gordon, N. J.; Evans, S. A., Jr. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 75, 47-50. Li, Y. F.; Hammerschmidt, F. Tetrahedron: Asymm. 1993, 4, 109-120. Wynberg, H.; Smaardijk, A. A. Tetrahedron Lett. 1983, 24, 5899-5900. Sum, V., Davies, A. J.; Kee, T. P. J. Chem. Soc., Chem. Commun. 1992, 1771-1773. Jacques, J.; Leclercq, M.; Brienne, M. J. Tetrahedron 1981, 37, 1727-1733. Heisler, A.; Rabiller, C.; Douillard, R.; Goalou, N.; Hägele, G.; Levayer, F. Tetrahedron: Asymm. 1993, 4, 959-960. Hoffmann, M. J. Prakt. Chem. 1990, 251-255. Gordon, N. J.; Evans, S. A., Jr. J. Org. Chem. 1993, 58, 5293-5294. Gajda, T. Tetrahedron: Asymm. 1994, 5, 1965-1972. Spilling, C. D.; Blazis, V. J.; Koeller, K. J. J. Org. Chem., 1995, 60, 931-940. Shibuya, S., Yokomatsu, T.; Yamagishi, T. Synlett 1995, 1035-1036.
17. Gordon, N. J.; Evans, S. A., Jr. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 75, 47-50. Li, Y. F.; Hammerschmidt, F. Tetrahedron: Asymm. 1993, 4, 109-120. Wynberg, H.; Smaardijk, A. A. Tetrahedron Lett. 1983, 24, 5899-5900. Sum, V., Davies, A. J.; Kee, T. P. J. Chem. Soc., Chem. Commun. 1992, 1771-1773. Jacques, J.; Leclercq, M.; Brienne, M. J. Tetrahedron 1981, 37, 1727-1733. Heisler, A.; Rabiller, C.; Douillard, R.; Goalou, N.; Hägele, G.; Levayer, F. Tetrahedron: Asymm. 1993, 4, 959-960. Hoffmann, M. J. Prakt. Chem. 1990, 251-255. Gordon, N. J.; Evans, S. A., Jr. J. Org. Chem. 1993, 58, 5293-5294. Gajda, T. Tetrahedron: Asymm. 1994, 5, 1965-1972. Spilling, C. D.; Blazis, V. J.; Koeller, K. J. J. Org. Chem., 1995, 60, 931-940. Shibuya, S., Yokomatsu, T.; Yamagishi, T. Synlett 1995, 1035-1036.
18. Gordon, N. J.; Evans, S. A., Jr. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 75, 47-50. Li, Y. F.; Hammerschmidt, F. Tetrahedron: Asymm. 1993, 4, 109-120. Wynberg, H.; Smaardijk, A. A. Tetrahedron Lett. 1983, 24, 5899-5900. Sum, V., Davies, A. J.; Kee, T. P. J. Chem. Soc., Chem. Commun. 1992, 1771-1773. Jacques, J.; Leclercq, M.; Brienne, M. J. Tetrahedron 1981, 37, 1727-1733. Heisler, A.; Rabiller, C.; Douillard, R.; Goalou, N.; Hägele, G.; Levayer, F. Tetrahedron: Asymm. 1993, 4, 959-960. Hoffmann, M. J. Prakt. Chem. 1990, 251-255. Gordon, N. J.; Evans, S. A., Jr. J. Org. Chem. 1993, 58, 5293-5294. Gajda, T. Tetrahedron: Asymm. 1994, 5, 1965-1972. Spilling, C. D.; Blazis, V. J.; Koeller, K. J. J. Org. Chem., 1995, 60, 931-940. Shibuya, S., Yokomatsu, T.; Yamagishi, T. Synlett 1995, 1035-1036.
19. Gordon, N. J.; Evans, S. A., Jr. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 75, 47-50. Li, Y. F.; Hammerschmidt, F. Tetrahedron: Asymm. 1993, 4, 109-120. Wynberg, H.; Smaardijk, A. A. Tetrahedron Lett. 1983, 24, 5899-5900. Sum, V., Davies, A. J.; Kee, T. P. J. Chem. Soc., Chem. Commun. 1992, 1771-1773. Jacques, J.; Leclercq, M.; Brienne, M. J. Tetrahedron 1981, 37, 1727-1733. Heisler, A.; Rabiller, C.; Douillard, R.; Goalou, N.; Hägele, G.; Levayer, F. Tetrahedron: Asymm. 1993, 4, 959-960. Hoffmann, M. J. Prakt. Chem. 1990, 251-255. Gordon, N. J.; Evans, S. A., Jr. J. Org. Chem. 1993, 58, 5293-5294. Gajda, T. Tetrahedron: Asymm. 1994, 5, 1965-1972. Spilling, C. D.; Blazis, V. J.; Koeller, K. J. J. Org. Chem., 1995, 60, 931-940. Shibuya, S., Yokomatsu, T.; Yamagishi, T. Synlett 1995, 1035-1036.
20. Gordon, N. J.; Evans, S. A., Jr. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 75, 47-50. Li, Y. F.; Hammerschmidt, F. Tetrahedron: Asymm. 1993, 4, 109-120. Wynberg, H.; Smaardijk, A. A. Tetrahedron Lett. 1983, 24, 5899-5900. Sum, V., Davies, A. J.; Kee, T. P. J. Chem. Soc., Chem. Commun. 1992, 1771-1773. Jacques, J.; Leclercq, M.; Brienne, M. J. Tetrahedron 1981, 37, 1727-1733. Heisler, A.; Rabiller, C.; Douillard, R.; Goalou, N.; Hägele, G.; Levayer, F. Tetrahedron: Asymm. 1993, 4, 959-960. Hoffmann, M. J. Prakt. Chem. 1990, 251-255. Gordon, N. J.; Evans, S. A., Jr. J. Org. Chem. 1993, 58, 5293-5294. Gajda, T. Tetrahedron: Asymm. 1994, 5, 1965-1972. Spilling, C. D.; Blazis, V. J.; Koeller, K. J. J. Org. Chem., 1995, 60, 931-940. Shibuya, S., Yokomatsu, T.; Yamagishi, T. Synlett 1995, 1035-1036.
21. Gordon, N. J.; Evans, S. A., Jr. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 75, 47-50. Li, Y. F.; Hammerschmidt, F. Tetrahedron: Asymm. 1993, 4, 109-120. Wynberg, H.; Smaardijk, A. A. Tetrahedron Lett. 1983, 24, 5899-5900. Sum, V., Davies, A. J.; Kee, T. P. J. Chem. Soc., Chem. Commun. 1992, 1771-1773. Jacques, J.; Leclercq, M.; Brienne, M. J. Tetrahedron 1981, 37, 1727-1733. Heisler, A.; Rabiller, C.; Douillard, R.; Goalou, N.; Hägele, G.; Levayer, F. Tetrahedron: Asymm. 1993, 4, 959-960. Hoffmann, M. J. Prakt. Chem. 1990, 251-255. Gordon, N. J.; Evans, S. A., Jr. J. Org. Chem. 1993, 58, 5293-5294. Gajda, T. Tetrahedron: Asymm. 1994, 5, 1965-1972. Spilling, C. D.; Blazis, V. J.; Koeller, K. J. J. Org. Chem., 1995, 60, 931-940. Shibuya, S., Yokomatsu, T.; Yamagishi, T. Synlett 1995, 1035-1036.
22. Gordon, N. J.; Evans, S. A., Jr. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 75, 47-50. Li, Y. F.; Hammerschmidt, F. Tetrahedron: Asymm. 1993, 4, 109-120. Wynberg, H.; Smaardijk, A. A. Tetrahedron Lett. 1983, 24, 5899-5900. Sum, V., Davies, A. J.; Kee, T. P. J. Chem. Soc., Chem. Commun. 1992, 1771-1773. Jacques, J.; Leclercq, M.; Brienne, M. J. Tetrahedron 1981, 37, 1727-1733. Heisler, A.; Rabiller, C.; Douillard, R.; Goalou, N.; Hägele, G.; Levayer, F. Tetrahedron: Asymm. 1993, 4, 959-960. Hoffmann, M. J. Prakt. Chem. 1990, 251-255. Gordon, N. J.; Evans, S. A., Jr. J. Org. Chem. 1993, 58, 5293-5294. Gajda, T. Tetrahedron: Asymm. 1994, 5, 1965-1972. Spilling, C. D.; Blazis, V. J.; Koeller, K. J. J. Org. Chem., 1995, 60, 931-940. Shibuya, S., Yokomatsu, T.; Yamagishi, T. Synlett 1995, 1035-1036.
23. Gordon, N. J.; Evans, S. A., Jr. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 75, 47-50. Li, Y. F.; Hammerschmidt, F. Tetrahedron: Asymm. 1993, 4, 109-120. Wynberg, H.; Smaardijk, A. A. Tetrahedron Lett. 1983, 24, 5899-5900. Sum, V., Davies, A. J.; Kee, T. P. J. Chem. Soc., Chem. Commun. 1992, 1771-1773. Jacques, J.; Leclercq, M.; Brienne, M. J. Tetrahedron 1981, 37, 1727-1733. Heisler, A.; Rabiller, C.; Douillard, R.; Goalou, N.; Hägele, G.; Levayer, F. Tetrahedron: Asymm. 1993, 4, 959-960. Hoffmann, M. J. Prakt. Chem. 1990, 251-255. Gordon, N. J.; Evans, S. A., Jr. J. Org. Chem. 1993, 58, 5293-5294. Gajda, T. Tetrahedron: Asymm. 1994, 5, 1965-1972. Spilling, C. D.; Blazis, V. J.; Koeller, K. J. J. Org. Chem., 1995, 60, 931-940. Shibuya, S., Yokomatsu, T.; Yamagishi, T. Synlett 1995, 1035-1036.
24. Gordon, N. J.; Evans, S. A., Jr. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 75, 47-50. Li, Y. F.; Hammerschmidt, F. Tetrahedron: Asymm. 1993, 4, 109-120. Wynberg, H.; Smaardijk, A. A. Tetrahedron Lett. 1983, 24, 5899-5900. Sum, V., Davies, A. J.; Kee, T. P. J. Chem. Soc., Chem. Commun. 1992, 1771-1773. Jacques, J.; Leclercq, M.; Brienne, M. J. Tetrahedron 1981, 37, 1727-1733. Heisler, A.; Rabiller, C.; Douillard, R.; Goalou, N.; Hägele, G.; Levayer, F. Tetrahedron: Asymm. 1993, 4, 959-960. Hoffmann, M. J. Prakt. Chem. 1990, 251-255. Gordon, N. J.; Evans, S. A., Jr. J. Org. Chem. 1993, 58, 5293-5294. Gajda, T. Tetrahedron: Asymm. 1994, 5, 1965-1972. Spilling, C. D.; Blazis, V. J.; Koeller, K. J. J. Org. Chem., 1995, 60, 931-940. Shibuya, S., Yokomatsu, T.; Yamagishi, T. Synlett 1995, 1035-1036.
25. Gordon, N. J.; Evans, S. A., Jr. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 75, 47-50. Li, Y. F.; Hammerschmidt, F. Tetrahedron: Asymm. 1993, 4, 109-120. Wynberg, H.; Smaardijk, A. A. Tetrahedron Lett. 1983, 24, 5899-5900. Sum, V., Davies, A. J.; Kee, T. P. J. Chem. Soc., Chem. Commun. 1992, 1771-1773. Jacques, J.; Leclercq, M.; Brienne, M. J. Tetrahedron 1981, 37, 1727-1733. Heisler, A.; Rabiller, C.; Douillard, R.; Goalou, N.; Hägele, G.; Levayer, F. Tetrahedron: Asymm. 1993, 4, 959-960. Hoffmann, M. J. Prakt. Chem. 1990, 251-255. Gordon, N. J.; Evans, S. A., Jr. J. Org. Chem. 1993, 58, 5293-5294. Gajda, T. Tetrahedron: Asymm. 1994, 5, 1965-1972. Spilling, C. D.; Blazis, V. J.; Koeller, K. J. J. Org. Chem., 1995, 60, 931-940. Shibuya, S., Yokomatsu, T.; Yamagishi, T. Synlett 1995, 1035-1036.
26. Gordon, N. J.; Evans, S. A., Jr. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 75, 47-50. Li, Y. F.; Hammerschmidt, F. Tetrahedron: Asymm. 1993, 4, 109-120. Wynberg, H.; Smaardijk, A. A. Tetrahedron Lett. 1983, 24, 5899-5900. Sum, V., Davies, A. J.; Kee, T. P. J. Chem. Soc., Chem. Commun. 1992, 1771-1773. Jacques, J.; Leclercq, M.; Brienne, M. J. Tetrahedron 1981, 37, 1727-1733. Heisler, A.; Rabiller, C.; Douillard, R.; Goalou, N.; Hägele, G.; Levayer, F. Tetrahedron: Asymm. 1993, 4, 959-960. Hoffmann, M. J. Prakt. Chem. 1990, 251-255. Gordon, N. J.; Evans, S. A., Jr. J. Org. Chem. 1993, 58, 5293-5294. Gajda, T. Tetrahedron: Asymm. 1994, 5, 1965-1972. Spilling, C. D.; Blazis, V. J.; Koeller, K. J. J. Org. Chem., 1995, 60, 931-940. Shibuya, S., Yokomatsu, T.; Yamagishi, T. Synlett 1995, 1035-1036.
27. Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104-106. The structure of ALB, which consists of Al, Li, and two BINOL units, has been unequivocally determined by X-ray analysis.
28. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656-6657.
29. Rath, N. P.; Spilling, C. D. Tetrahedron Lett. 1994, 35, 227-230. Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymm. 1993, 4, 1783-1784.
30. Rath, N. P.; Spilling, C. D. Tetrahedron Lett. 1994, 35, 227-230. Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymm. 1993, 4, 1783-1784.
31. The optical purities of all of the products were determined by chiral HPLC (DAICEL CHIRALPAK AS or AD), and the absolute configurations of all of the products were determined by the Mosher method.
32. 2, 20% acetone/hexane) gave the α-hydroxy phosphonate 3 (78 mg, 90%) with 85% ee as a colorless solid (mp = 86-87°C).
33. The use of diethyl phosphite and dibutyl phosphite gave the corresponding phosphonates with 73% ee, 39% yield and 67% ee, 42% yield, respectively.
34. For the discussion of the multifunctional activities of heterobimetallic asymmetric catalysts, see: Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198.
35. The asymmetric catalyst 21 was prepared from ALB by treatment with trimethylsilyl chloride (1.2 equiv) in THF at -78°C. This catalyst was then used in toluene as described in ref 10. (Equation Presented)