Asymmetric Synthesis of Chiral, Nonracemic Dialkyl-α-Hydroxyalkylphosphonates via a (-)-Chlorodiisopinocampheylborane (Ipc2B-Cl) Reduction

Tetrahedron Asymmetry

Volumn 7, Issue 1, 1996, Pages 89-94

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

^a GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030028744     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(95)00424-6     Document Type: Article

References (31)

1. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Tetrahedron Lett. 1990, 31, 5587 and 5591.
2. 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.
3. Stowasser, B.; Budt, K.; Jian-Qi, L.; Peyman, A.; Ruppert, D.; Tetrahedron Lett. 1992, 33, 6625.
4. Kafarski, P.; Lejczak, B.; Phosphorus, Sulfur and Silicon, 1991, 63, 193.
5. Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron: Asymmetry 1993, 4, 1401. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; J. Org. Chem. 1994, 59, 7930.
6. Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron: Asymmetry 1993, 4, 1401. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; J. Org. Chem. 1994, 59, 7930.
7. Devitt, P. G.; Kee, T. P.; J. Chem. Soc. Perkin Trans. 1, 1994, 3169 and 3182. - Blazis, V. J.; Koeller, K. J.; Spilling, C. D.; J. Org. Chem. 1995, 60, 931. - Blazis, V. J., Koeller, K. J.; Spilling, C. D.; Tetrahedron:Asymmetry 1994, 5, 499.
8. Devitt, P. G.; Kee, T. P.; J. Chem. Soc. Perkin Trans. 1, 1994, 3169 and 3182. - Blazis, V. J.; Koeller, K. J.; Spilling, C. D.; J. Org. Chem. 1995, 60, 931. - Blazis, V. J., Koeller, K. J.; Spilling, C. D.; Tetrahedron:Asymmetry 1994, 5, 499.
9. Devitt, P. G.; Kee, T. P.; J. Chem. Soc. Perkin Trans. 1, 1994, 3169 and 3182. - Blazis, V. J.; Koeller, K. J.; Spilling, C. D.; J. Org. Chem. 1995, 60, 931. - Blazis, V. J., Koeller, K. J.; Spilling, C. D.; Tetrahedron:Asymmetry 1994, 5, 499.
10. Rath, N. P.; Spilling, C. D.; Tetrahedron Lett. 1994, 35, 227. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1779 and 1783. - Smaardijk, A. A.; Noorda, S.; van Bolhuis, F.; Wynberg, H.; Tetrahedron Lett. 1985, 26, 493. - Wynberg, H.; Smaardijk, A. A.; Tetrahedron Lett. 1983, 24, 5899.
11. Rath, N. P.; Spilling, C. D.; Tetrahedron Lett. 1994, 35, 227. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1779 and 1783. - Smaardijk, A. A.; Noorda, S.; van Bolhuis, F.; Wynberg, H.; Tetrahedron Lett. 1985, 26, 493. - Wynberg, H.; Smaardijk, A. A.; Tetrahedron Lett. 1983, 24, 5899.
12. Rath, N. P.; Spilling, C. D.; Tetrahedron Lett. 1994, 35, 227. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1779 and 1783. - Smaardijk, A. A.; Noorda, S.; van Bolhuis, F.; Wynberg, H.; Tetrahedron Lett. 1985, 26, 493. - Wynberg, H.; Smaardijk, A. A.; Tetrahedron Lett. 1983, 24, 5899.
13. Rath, N. P.; Spilling, C. D.; Tetrahedron Lett. 1994, 35, 227. - Yokomatsu, T.; Yamagishi, T.; Shibuya, S.; Tetrahedron:Asymmetry 1993, 4, 1779 and 1783. - Smaardijk, A. A.; Noorda, S.; van Bolhuis, F.; Wynberg, H.; Tetrahedron Lett. 1985, 26, 493. - Wynberg, H.; Smaardijk, A. A.; Tetrahedron Lett. 1983, 24, 5899.
14. Drescher, M.; Li, Y.-F.; Hammerschmidt, Tetrahedron, 1995, 51, 4933. - Hammerschmidt, F.; Völlenkle, H.; Liebigs Ann. Chem. 1989, 577.
15. Drescher, M.; Li, Y.-F.; Hammerschmidt, Tetrahedron, 1995, 51, 4933. - Hammerschmidt, F.; Völlenkle, H.; Liebigs Ann. Chem. 1989, 577.
16. Meier, C.; Laux, W. H. G.; Tetrahedron:Asymmetry 1995, 6, 1089.
17. Gajda, T.; Tetrahedron:Asymmetry 1994, 5, 1965.
18. Creary, X.; Geiger, C. C.; Hilton, K.; J. Am. Chem. Soc. 1983, 105, 2851.
19. Meier, C; Angew. Chem. 1993, 105, 1854; Angew. Chem. Int. Ed. Engl. 1993, 32, 1704. - Meier, C.; Laux, W. H. G.; Habel, L. W.; Balzarini, J.; De Clercq, E.; Nucl. Nucl. 1995, 14, 759. - Meier, C.; Habel, L. W.; Balzarini, J.; De Clercq, E.; Liebigs Ann. Chem. 1995, in press.
20. Meier, C; Angew. Chem. 1993, 105, 1854; Angew. Chem. Int. Ed. Engl. 1993, 32, 1704. - Meier, C.; Laux, W. H. G.; Habel, L. W.; Balzarini, J.; De Clercq, E.; Nucl. Nucl. 1995, 14, 759. - Meier, C.; Habel, L. W.; Balzarini, J.; De Clercq, E.; Liebigs Ann. Chem. 1995, in press.
21. Meier, C; Angew. Chem. 1993, 105, 1854; Angew. Chem. Int. Ed. Engl. 1993, 32, 1704. - Meier, C.; Laux, W. H. G.; Habel, L. W.; Balzarini, J.; De Clercq, E.; Nucl. Nucl. 1995, 14, 759. - Meier, C.; Habel, L. W.; Balzarini, J.; De Clercq, E.; Liebigs Ann. Chem. 1995, in press.
22. Meier, C; Angew. Chem. 1993, 105, 1854; Angew. Chem. Int. Ed. Engl. 1993, 32, 1704. - Meier, C.; Laux, W. H. G.; Habel, L. W.; Balzarini, J.; De Clercq, E.; Nucl. Nucl. 1995, 14, 759. - Meier, C.; Habel, L. W.; Balzarini, J.; De Clercq, E.; Liebigs Ann. Chem. 1995, in press.
23. Meier, C.; Mauritz, R.; Nucl. Nucl. 1995, 14, 803.
24. Meier, C.; Laux, W. H. G.; Bats, J. W; Liebigs Ann. Chem. 1995, in press. - Meier, C.; Laux, W. H. G.; Tetrahedron, in press.
25. Meier, C.; Laux, W. H. G.; Bats, J. W; Liebigs Ann. Chem. 1995, in press. - Meier, C.; Laux, W. H. G.; Tetrahedron, in press.
26. Arbusov, B. A.; Zoroatrova, V. M.; Tudrin, G. A.; Fuzhenkova, A. V.; Izv. Akad. Nauk S.S.S.R. (Transl.), 1974, 23, 2541-2542. - Berlin, K. D.; Taylor, H. A.; J. Am. Chem. Soc. 1964, 86, 3862.
27. Arbusov, B. A.; Zoroatrova, V. M.; Tudrin, G. A.; Fuzhenkova, A. V.; Izv. Akad. Nauk S.S.S.R. (Transl.), 1974, 23, 2541-2542. - Berlin, K. D.; Taylor, H. A.; J. Am. Chem. Soc. 1964, 86, 3862.
28. Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C.; Tetrahedron 1993, 49, 1725.
29. In contrast to the other reaction in this case the precipitation (see General Experimental Procedure) using diethanolamine was omitted because of the instability of 2i. The reaction mixture was directly isolated by chromotography.
30. Stereochemistry was assigned by a X-ray crystal structure of 2d.
31. Brown, H. C.; Chandrasekharan, J.; Ramachandran, P. V.; J. Org. Chem. 1986, 51, 3394.