Enantioselective synthesis of α-hydroxy phosphonates using the LaLi3tris(binaphthoxide) catalyst (LLB), prepared by an improved method

Tetrahedron Letters

Volumn 38, Issue 15, 1997, Pages 2717-2720

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

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA HYDROXYPHOSPHONIC ACID DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030907801     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00437-1     Document Type: Article

References (46)

1. a) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5587-5590.
2. b) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5591-5594.
3. c) 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.
4. d) 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.
5. e) Stowasser, B.; Budt, K-H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625-6628.
6. a) Hammerschmidt, F.; Völlenkle, H. Liebigs Ann. Chem. 1989, 577-583.
7. b) Yokomatsu, T.; Shibuya, S. Tetrahedron: Asymmetry 1992, 3, 377-378.
8. c) Barald, P. G.; Guameri, M.; Moroder, F.; Pollini, G. P.; Simoni, D. Synthesis 1982, 653-654.
9. d) Maier, L. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 76, 379.
10. e) Ohler, E.; Kotzinger, S. Synthesis 1993, 497-502 and references cited therein.
11. f) Cao, X.; Mjalli, M. M. Tetrahedron Lett. 1996, 37, 6073-6076.
12. g) For a review see; Kafarski, P; Lejczak, B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63, 193-215.
13. a) 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.
14. b) 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.
15. c) 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. a) Gordon, N. J.; Evans, Jr., S. A. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 75, 47-50.
17. b) Li, Y. F.; Hammerschmidt, F. Tetrahedron: Asymmetry 1993, 4, 109-120.
18. c) Wynberg, H.; Smaardijk, A. A. Tetrahedron Lett. 1983, 24, 5899-5900.
19. d) Sum, V.; Davies, A. J.; Kee, T. P. J. Chem. Soc., Chem. Commun. 1992, 1771-1773.
20. e) Jacques, J.; Leclercq, M.; Brienne, M. J. Tetrahedron 1981, 37, 1727-1733.
21. f) Heisler, A.; Rabiller, C.; Douillard, R.; Goalou, N.; Hägele, G.; Levayer, F. Tetrahedron: Asymmetry 1993, 4, 959-960.
22. g) Hoffmann, M. J. Prakt. Chem. 1990, 251-255.
23. h) Gordon, N. J.; Evans, Jr. S. A. J. Org. Chem. 1993, 58, 5293-5294.
24. i) Gajda, T. Tetrahedron: Asymmetry 1994, 5, 1965-1972.
25. j) Blazis, V. J.; Koeller, K. J.; Spilling, C.D. J. Org. Chem., 1995, 60, 931-940.
26. k) Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Synlett 1995, 1035-1036.
27. a) Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1993, 4, 1783-1784.
28. b) Rath, N.P.; Spilling, C. D. Tetrahedron Lett. 1994, 35, 227-230.
29. a) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420.
30. b) Sasai, H.; Suzuki, T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854.
31. c) Sasai, H.; Itoh, N.; Suzuki, T.; Shibasaki, M. Tetrahedron Lett. 1993. 34, 855-858.
32. d) Sasai, H.; Suzuki, T.; Itoh, N.; Arai, S.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 2657-2660.
33. e) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372-10373.
34. f) Sasai, H.; Kim, W.-S.; Suzuki, T.; Shibasaki, M.; Mitsuda, M.; Hasegawa, J.; Ohashi, T. Tetrahedron Lett. 1994, 35, 6123-6126.
35. g) Sasai, H.; Yamada, Y. M. A.; Suzuki, T.; Shibasaki, M. Tetrahedron 1994, 50, 12313-12318.
36. h) Sasai, H.; Tokunaga, T.; Watanabe, S.; Suzuki, T.; Itoh, N.; Shibasaki, M. J. Org. Chem. 1995, 60, 7388-7389.
37. 2O (3.12 g, 8.40 mmol) in THF (100 mL) was sonicated for 30 min at room temperature. To this suspension was then added the above-prepared solution of dilithium binaphthoxide and 0.52 N NaO-t-Buin THF (4.85 mL, 2.52 mmol), dropwise at room temperature. After being stirred vigorously overnight at room temperature and then for 48 h at 50 °C, the reaction mixture was allowed to stand at room temperature. The resulting supernatant was used as an asymmetric catalyst (0.03 M). Sasai, H.; Watanabe, S.; Shibasaki, M. Enantiomer, in press.
38. The absolute configurations of the products except for 12 were determined by the Mosher method.
39. 3 derived LLB gave 2 in 45% ee (83% yield) even at -78 °C with a slow addition of 1. The optical purity of 2 was increased (74% ee, 88% yield) when pumping dried LLB, all the sol vent of LLB, was removed by pumping up and then redissolved in THF, was utilized as a catalyst.
40. Arai, T.; Bougauchi, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926-2927.
41. a) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656-6657.
42. b) Groger, H.; Saida, T.; Arai, S.; Martens, J.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 9291-9292.
43. a) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104-106.
44. b) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J., 1996, 2, 1368-1372.
45. In the case of ALB catalyzed hydrophosphonylations, slow addition of aldehydes didn't improve ees.
46. 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. See, also references 6h and 12a.