Enantioselective synthesis of diisopropyl α-, β-, and γ-hydroxyarylalkylphosphonates from ketophosphonates: A study on the effect of the phosphonyl group

Tetrahedron

Volumn 52, Issue 2, 1996, Pages 589-598

  Meier, Chris ^a   Laux, Wolfgang H G ^a  

^a GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REDUCTION; STRUCTURE ACTIVITY RELATION; TECHNIQUE;

EID: 0030058694     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00855-1     Document Type: Article

References (52)

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.
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.
3. Sikorski, J. A.; Miller, M. J.; Braccolini, 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 and Silicon, 1993, 76, 115-118.
4. Stowasser, B.; Budt, K.; Jian-Qi, L.; Peyman, A.; Ruppert, D.; Tetrahedron Lett. 1992, 33, 6625-6628.
5. Kametami, T.; Kigasawa, K.; Hiragi, M.; Wasisaka, K.; Saga, S.; Tanigawa, K.; Suzuki, Y.; Fukawa, K.; Irino, O.; Saita, O.; Yambe, S.; Heterocycles 1981, 16, 1205-1211. - Kafarski, P.; Lejczak, B.; Phosphorus, Sulfur and Silicon, 1991, 63, 193-215.
6. Kametami, T.; Kigasawa, K.; Hiragi, M.; Wasisaka, K.; Saga, S.; Tanigawa, K.; Suzuki, Y.; Fukawa, K.; Irino, O.; Saita, O.; Yambe, S.; Heterocycles 1981, 16, 1205-1211. - Kafarski, P.; Lejczak, B.; Phosphorus, Sulfur and Silicon, 1991, 63, 193-215.
7. Dhawan, B.; Redmore, D.; Phosphorus and Sulfur, 1987, 32, 119-144.
8. Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1401-1404. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; J. Org. Chem. 1994, 59, 7930-7933
9. Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1401-1404. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; J. Org. Chem. 1994, 59, 7930-7933
10. Devitt, P. G.; Kee, T. P.; J. Chem. Soc. Perkin Trans. 1, 1994, 31692-3181. - Sum, V.; Baird, C. A.; Kee, T. P.; Thornton-Pett, M.; J. Chem. Soc. Perkin Trans. 1, 1994, 3182-3200. - Sum, V.; Kee, T. P.; Thornton-Pett, M.; J. Chem. Soc. Chem. Commun. 1994, 743-744. - Blazis, V. J.; Koeller, K. J.; Spilling, C. D.; J. Org. Chem. 1995, 60, 931-940. - Blazis, V. J.; Koeller, K. J.; Spilling, C. D.; Tetrahedron:Asymmetry 1994, 5, 499-502.
11. Devitt, P. G.; Kee, T. P.; J. Chem. Soc. Perkin Trans. 1, 1994, 31692-3181. - Sum, V.; Baird, C. A.; Kee, T. P.; Thornton-Pett, M.; J. Chem. Soc. Perkin Trans. 1, 1994, 3182-3200. - Sum, V.; Kee, T. P.; Thornton-Pett, M.; J. Chem. Soc. Chem. Commun. 1994, 743-744. - Blazis, V. J.; Koeller, K. J.; Spilling, C. D.; J. Org. Chem. 1995, 60, 931-940. - Blazis, V. J.; Koeller, K. J.; Spilling, C. D.; Tetrahedron:Asymmetry 1994, 5, 499-502.
12. Devitt, P. G.; Kee, T. P.; J. Chem. Soc. Perkin Trans. 1, 1994, 31692-3181. - Sum, V.; Baird, C. A.; Kee, T. P.; Thornton-Pett, M.; J. Chem. Soc. Perkin Trans. 1, 1994, 3182-3200. - Sum, V.; Kee, T. P.; Thornton-Pett, M.; J. Chem. Soc. Chem. Commun. 1994, 743-744. - Blazis, V. J.; Koeller, K. J.; Spilling, C. D.; J. Org. Chem. 1995, 60, 931-940. - Blazis, V. J.; Koeller, K. J.; Spilling, C. D.; Tetrahedron:Asymmetry 1994, 5, 499-502.
13. Devitt, P. G.; Kee, T. P.; J. Chem. Soc. Perkin Trans. 1, 1994, 31692-3181. - Sum, V.; Baird, C. A.; Kee, T. P.; Thornton-Pett, M.; J. Chem. Soc. Perkin Trans. 1, 1994, 3182-3200. - Sum, V.; Kee, T. P.; Thornton-Pett, M.; J. Chem. Soc. Chem. Commun. 1994, 743-744. - Blazis, V. J.; Koeller, K. J.; Spilling, C. D.; J. Org. Chem. 1995, 60, 931-940. - Blazis, V. J.; Koeller, K. J.; Spilling, C. D.; Tetrahedron:Asymmetry 1994, 5, 499-502.
14. Devitt, P. G.; Kee, T. P.; J. Chem. Soc. Perkin Trans. 1, 1994, 31692-3181. - Sum, V.; Baird, C. A.; Kee, T. P.; Thornton-Pett, M.; J. Chem. Soc. Perkin Trans. 1, 1994, 3182-3200. - Sum, V.; Kee, T. P.; Thornton-Pett, M.; J. Chem. Soc. Chem. Commun. 1994, 743-744. - Blazis, V. J.; Koeller, K. J.; Spilling, C. D.; J. Org. Chem. 1995, 60, 931-940. - Blazis, V. J.; Koeller, K. J.; Spilling, C. D.; Tetrahedron:Asymmetry 1994, 5, 499-502.
15. Pudovik, A. N.; Konovalova, I. V.; Synthesis 1979, 81-96.
16. Rath, N. P.; Spilling, C. D.; Tetrahedron Lett. 1994, 35, 227-230. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1779-1782. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1783-1784. - Smaardijk, A. A.; Noorda, S.; van Bolhuis, F.; Wynberg, H.; Tetrahedron Lett. 1985, 26, 493-496. - Wynberg, H.; Smaardijk, A. A.; Tetrahedron Lett. 1983, 24, 5899-5900.
17. Rath, N. P.; Spilling, C. D.; Tetrahedron Lett. 1994, 35, 227-230. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1779-1782. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1783-1784. - Smaardijk, A. A.; Noorda, S.; van Bolhuis, F.; Wynberg, H.; Tetrahedron Lett. 1985, 26, 493-496. - Wynberg, H.; Smaardijk, A. A.; Tetrahedron Lett. 1983, 24, 5899-5900.
18. Rath, N. P.; Spilling, C. D.; Tetrahedron Lett. 1994, 35, 227-230. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1779-1782. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1783-1784. - Smaardijk, A. A.; Noorda, S.; van Bolhuis, F.; Wynberg, H.; Tetrahedron Lett. 1985, 26, 493-496. - Wynberg, H.; Smaardijk, A. A.; Tetrahedron Lett. 1983, 24, 5899-5900.
19. Rath, N. P.; Spilling, C. D.; Tetrahedron Lett. 1994, 35, 227-230. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1779-1782. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1783-1784. - Smaardijk, A. A.; Noorda, S.; van Bolhuis, F.; Wynberg, H.; Tetrahedron Lett. 1985, 26, 493-496. - Wynberg, H.; Smaardijk, A. A.; Tetrahedron Lett. 1983, 24, 5899-5900.
20. Rath, N. P.; Spilling, C. D.; Tetrahedron Lett. 1994, 35, 227-230. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1779-1782. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1783-1784. - Smaardijk, A. A.; Noorda, S.; van Bolhuis, F.; Wynberg, H.; Tetrahedron Lett. 1985, 26, 493-496. - Wynberg, H.; Smaardijk, A. A.; Tetrahedron Lett. 1983, 24, 5899-5900.
21. Gajda, T.; Tetrahedron:Asymmetry 1994, 5, 1965-1972.
22. Kitamura, M.;Tokunaga, M.; Noyori, R.; J. Am. Chem. Soc. 1995, 117, 2931-2932.
23. Drescher, M.; Li, Y.-F.; Hammerschmidt, Tetrahedron, 1995, 57, 4933-4946. - Hammerschmidt, F.; Völlenkle, H.; Liebigs Ann. Chem. 1989, 577-583.
24. Drescher, M.; Li, Y.-F.; Hammerschmidt, Tetrahedron, 1995, 57, 4933-4946. - Hammerschmidt, F.; Völlenkle, H.; Liebigs Ann. Chem. 1989, 577-583.
25. Meier, C.; Angew. Chem. 1993, 105, 1854-1856, Angew. Chem. Int. Ed. Engl. 1993, 32, 1704-1706. - Meier, C.; Laux, W. H. G.; Habel, L.; Balzarini, J.; De Clercq, E.; Nucl. Nucl. 1995, 14, 759-762. - Meier, C.; Habel, L. W.; Baizarini, J.; De Clercq, E.; Liebigs Ann. Chem. 1995, submitted.
26. Meier, C.; Angew. Chem. 1993, 105, 1854-1856, Angew. Chem. Int. Ed. Engl. 1993, 32, 1704-1706. - Meier, C.; Laux, W. H. G.; Habel, L.; Balzarini, J.; De Clercq, E.; Nucl. Nucl. 1995, 14, 759-762. - Meier, C.; Habel, L. W.; Baizarini, J.; De Clercq, E.; Liebigs Ann. Chem. 1995, submitted.
27. Meier, C.; Angew. Chem. 1993, 105, 1854-1856, Angew. Chem. Int. Ed. Engl. 1993, 32, 1704-1706. - Meier, C.; Laux, W. H. G.; Habel, L.; Balzarini, J.; De Clercq, E.; Nucl. Nucl. 1995, 14, 759-762. - Meier, C.; Habel, L. W.; Baizarini, J.; De Clercq, E.; Liebigs Ann. Chem. 1995, submitted.
28. Meier, C.; Angew. Chem. 1993, 105, 1854-1856, Angew. Chem. Int. Ed. Engl. 1993, 32, 1704-1706. - Meier, C.; Laux, W. H. G.; Habel, L.; Balzarini, J.; De Clercq, E.; Nucl. Nucl. 1995, 14, 759-762. - Meier, C.; Habel, L. W.; Baizarini, J.; De Clercq, E.; Liebigs Ann. Chem. 1995, submitted.
29. Meier, C.; Mauritz, R.; Nucl. Nucl. 1995, 14, 803-804.
30. Meier, C.; Laux, W. H. G.; Tetrahedron:Asymmetry 1995, 6, 1089-1092.
31. Meier, C.; Laux, W. H. G.; Bats, J. W.; Liebigs Ann. Chem. 1995, in press.
32. For a biological application for γ-hydroxyalkylphosphonates: Mori, I.; Iwasaki, G.; Kimura, Y.; Matsunga, S.-I.; Ogawa, A.; Nakano, T.; Buser, H-P.; Hatano, M.; Tada, S.; Hayakawa, K.; J. Am. Chem. Soc. 1995, 117, 4411-4412.
33. Arbusov, B. A.; Zoroatrova, V. M.; Tudrin, G. A.; Fuzhenkova, A. V.; Izv. Akad. Nauk S.S.S.R. (Transl.), 1974, 23, 2541-2542.
34. Corey, E. J.; Gras, J.-L.; Ulrich, P.; Tetrahedron Lett. 1976, 17, 809-812.
35. Corey, E. J.; Link, J. O.; J. Am. Chem. Soc. 1992, 114, 1906-1908.
36. Control experiments have shown that within 7 days at -80 °C only 10-15% of the starting materials 1 were reduced to yield the racemic α-hydroxyphosphonates 4.
37. Corey, E. J.; Link, J. O.; Tetrahedron Lett. 1992, 33, 4141-4144.
38. 31P NMR spectroscopy and showed satisfactory analytical data.
39. Hammerschmidt, F.; Li, Y.-F.; Tetrahedron 1994, 50, 10253-10264.
40. The absolute configuration of chiral, nonracemic 4c was determined using the anormal X-ray diffraction method introduced by Bijvoet, J.M.; Peerdeman, A. F.; van Bommel, A.J.; Nature 1951, 168, 271-272. The single crystals were obtained from a petroleum ether 60/80 solution. Full crystallographic data are available from the Fachinformationszentrum (FIZ), Karlsruhe, Gesellschaft für wissenschaftlich-technische Information mbH, D-76344 Eggenstein-Leopoldshafen, on quoting the depository number CSD-58960. A plot is shown beside.
41. 31P NMR spectrum. We knew before that the (1S)-(-)-camphanic acid ester of racemic 6 showed two well separated signals.
42. + value: Creary, X.; Geiger, C. C.; Hilton, K.; J. Am. Chem. Soc. 1983, 105, 2851-2858.
43. 16.
44. Control experiments at -20°C showed that only a very small amount of the ketones 1 was reduced by catecholborane within 8 h.
45. Evans, D. A.; Scott, S. G.; Gagné, M. R.; Muci, A. R.; J. Am. Chem. Soc. 1993, 115, 9800-9801.
46. Berlin, K. D.; Taylor, H. A.; J. Am. Chem. Soc. 1964, 86, 3862-3866.
47. Hayashi, T.; Matsumoto, Y.; Ito, Y.; Tetrahedron: Asymmetry 1991, 2, 601-612.
48. Pickard, S. T.; Smith, H. E.; J. Am. Chem. Soc. 1990, 112, 5741-5747.
49. Rae, I. D.; Burgess, D. A.; Bombaci, S.; Baron, M. L.; Woolcock, M. L.; Aust. J. Chem. 1984, 37, 1437-1446.
50. Resnick, S. M.; Torok, D. S.; Gibson, D. T.; J. Org. Chem. 1995, 60, 3546-3549.
51. Hayashi, T.; Matsumoto, Y.; Ito, Y.; J. Am. Chem. Soc. 1989, 111, 3426-3428.
52. Brown, H. C.; Cho, B. T.; Park, W. S.; J. Org. Chem. 1988, 53, 1231-1238.