A superior method for the reduction of secondary phosphine oxides

Organic Letters

Volumn 7, Issue 19, 2005, Pages 4277-4280

  Busacca, Carl A ^a   Lorenz, Jon C ^a   Grinberg, Nelu ^a   Haddad, Nizar ^a   Hrapchak, Matt ^a   Latli, Bachir ^a   Lee, Heewon ^a   Sabila, Paul ^a   Saha, Anjan ^a   Sarvestani, Max ^a   Shen, Sherry ^a   Varsolona, Richard ^a   Wei, Xudong ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM; LIGAND; OXIDE; PHOSPHINE; PHOSPHINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

ALUMINUM; LIGANDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; OXIDES; PHOSPHINES;

EID: 25444499193     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0517832     Document Type: Article

References (46)

1. For examples, see: (a) Grim, S. O.; Satek, L. C. J. Inorg. Nucl. Chem. 1977, 39, 499.
2. (b) Gatrone, R. C.; Dietz, M. L.; Horwitz, E. P. Solv. Extr. Ion Exch. 1993, 11 (3), 411.
3. (a) Li, G. Y. J. Organomet. Chem. 2002, 653 (1/2), 63.
4. (b) Jiang, X.-b.; Minnaard, A. J.; Hessen, B.; Feringa, B. L.; Duchateau, A. L. L.; Andrien, J. G. O.; Boogers, J. A. F.; de Vries, J. G. Org. Lett. 2003, 5 (9), 1503.
5. (c) Börner, A.; Dubrovina, N. V.; Angew. Chem., Int. Ed. 2004, 43 (44), 5883.
6. NAr: (a) Williams, J. M. J.; Coote, S. J.; Dawson, G. J.; Frost, C. G. Synlett 1993, 509.
7. N2: (b) Sakai, T.; Kodama, T.; Fujimoto, T.; Ohta, K.; Yamamoto, I.; Kakehi, A. J. Org. Chem. 1994, 59 (23), 7144
8. (c) Heidel, H.; Huttner, G.; Helmchen, G. Z. Naturforsch. B 1993, 48 (11), 1681.
9. (d) Imamoto, T.; Oshiki, T.; Onozawa, T.; Sato, K. J. Am. Chem. Soc. 1990, 112 (13), 5244.
10. Michael: (e) Blinn, D. A.; Button, R. S.; Farazi, V.; Neeb, M. K.; Tapley, C. L. J. Organomet. Chem. 1990, 393 (1), 143.
11. (f) Lavenot, L.; Bortoletto, M. H.; Roucoux, A.; Larpent, C.; Patin, H. J. Organomet. Chem. 1996, 509 (1), 9.
12. Hydrophosphination: (g) Shulyupin, M. O.; Kazankova, M. A.; Beletskaya, I. P. Org. Lett. 2002, 4 (5), 761.
13. (h) Kawaoka, A. M.; Marks, T. J. J. Am. Chem. Soc. 2004, 126 (40), 12764.
14. Cross-coupling: (i) Herd, O.; Hessler, A.; Hingst, M.; Tepper, M.; Stelzer, O. J. Organomet. Chem. 1996, 522, 69.
15. (j) Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1994, 59 (23), 7180
16. (k) Kraatz, H.-B.; Pletsch, A. Tetrahedron: Asymmetry 2000, 11, 1617.
17. (l) Hillhouse, J. H. U. S. Pat. 5,550,295, 1996.
18. Busacca, C. A. U. S. Pat. 6,316,620, 2001; European Patent 1218388. Boehringer-Ingelheim Phosphinoimidazolines.
19. (a) Busacca, C. A.; Grossbach, D.; Campbell, S. J.; Dong, Y.; Eriksson, M. C.; Harris, R. E.; Jones, P.-J.; Kim, J.-Y.; Lorenz, J. C.; McKellop, K. B.; O'Brien, E. M.; Qiu, F.; Simpson, R. D.; Smith, L.; So, R. C.; Spinelli, E. M.; Vitous, J.; Zavattaro, C. J. Org. Chem. 2004, 69 (16), 5187.
20. (b) Busacca, C. A.; Grossbach, D.; So, R. C.; O'Brien, E. M.; Spinelli, E. M. Org. Lett. 2003, 5 (4), 595.
21. (c) Menges, F.; Neuburger, M.; Pfaltz, A. Org. Lett. 2002, 4 (26), 4713.
22. (d) Boland, N. A.; Casey, M.; Hynes, S. J.; Matthews, J. W.; Smyth, M. P. J. Org. Chem. 2002, 67 (11), 3919.
23. (e) Guiu, E.; Claver, C.; Benet-Buchholz, J.; Castillon, S. Tetrahedron: Asymmetry 2004, 15 (21), 3365.
24. (a) Rajanbabu, T. V.; Casalnuovo, A. L.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116 (22), 9869.
25. (b) Lam, H.; Aldous, D. J.; Hii, K. K. Tetrahedron Lett. 2003, 44 (28), 5213.
26. Livinghouse, T.; McKinstry, L. Tetrahedron 1994, 50 (21), 6145.
27. (a) Dong, X.; Erkey, C. J. Mol. Catal. A 2004, 211, 73.
28. (b) Elding, L. I.; Kellenberger, B.; Venanzi, L. M. Helv. Chim. Acta 1983, 66(6), 1676.
29. (a) Hayashi, T.; Hirate, S.; Kitayama, K.; Tsuji, H.; Torii, A.; Uozumi, Y. J. Org. Chem. 2001, 66 (4), 1441.
30. (b) Wu, H.-C.; Yu, J.-Q.; Spencer, J. B. Org. Lett. 2004, 6 (25), 4675.
31. (a) Kapoor, P. N.; Venanzi, L. M. HeIv. Chim. Acta 1977, 60 (277), 2824.
32. (b) Fehring, V.; Kadyrov, R.; Ludwig, M.; Holz, J.; Haage, K.; Selke, R. J. Organomet. Chem. 2001, 1-2, 120.
33. (c) Miller, P. W.; Nieuwenhuyzen, M.; Xu, X.; James, S. L. Chem. Commun. 2002, 18, 2008.
34. P-H = 203 Hz.
35. Pietrusiewicz, K. M.; Stankevic, M. Synlett 2003, 7, 1012.
36. Reisch, M. Chem. Eng. News 2002, 80 (26), 7.
37. Busacca, C. A.; Lorenz, J. C. U. S.Pat. Appl. Ser. No. 11/034,089 Jan 13, 2004; Int. Appl. No. PCT/US05/01526.
38. GB 1,520,237, Appl. No. 18850/77, 1977.
39. For reviews see (a) Monakov, Y. B.; Sabirov, Z. M.; Urazbaev, V.; Zaikov, G. E. Polymer yearbook 2003, 18, 75.
40. (b) Monakov, Y. B.; Sabirov, Z. M.; Zaikov, G. E. New. Dev. Chem. Biochem. 2003, 53.
41. See also (c) Natta, G.; Mazzanti, G.; Giorgio, D.; Gino, S.; Sartori, G.; Motroni, G. IT Pat. 718796, 1966.
42. (d) Ziegler, K. Chem. Ber. 1964, 76, 545.
43. (a) Hansch, C.; Leo, A.; Unger, S. H.; Kim, N. H.; Nikaitani, D.; Lien, E. J. J. Med. Chem. 1973, 16 (11), 1207.
44. P-H = 206 Hz.
45. Chemglass Catal. No. AF-0542-22; AF-0542-25.
46. Photographs of the glassware are found in the Supporting Information.