Pallado-catalysed P-arylations and P-vinylation of 2-hydrogeno-2-oxo-1,4,2- oxazaphosphinanes

Tetrahedron

Volumn 61, Issue 29, 2005, Pages 7029-7036

  Pirat, Jean Luc ^a   Monbrun, Jérôme ^a   Virieux, David ^a   Cristau, Henri Jean ^a  

^a Laboratoire de Chimie Macromoleculaire UMR 5076   (France)

Author keywords

Aminoalkylarylphosphinic acid; Arylation; Arylphosphinate; Pallado catalyse; Vinylation

Indexed keywords

2 OXO 2,3,5,6 TETRAPHENYL 1,4,2 OXAZAPHOSPHINANE; 2 OXO 3,5,6 TRIPHENYL 2 (2 PYRIDYL) 1,4,2 OXAZAPHOSPHINANE; 2 OXO 3,5,6 TRIPHENYL 2 (2 THIENYL) 1,4,2 OXAZAPHOSPHINANE; 2 OXO 3,5,6 TRIPHENYL 2 (4 BROMOPHENYL) 1,4,2 OXAZAPHOSPHINANE; 2 OXO 3,5,6 TRIPHENYL 2 (4 METHOXYPHENYL) 1,4,2 OXAZAPHOSPHINANE; 2 OXO 3,5,6 TRIPHENYL 2 STYRYL 1,4,2 OXAZAPHOSPHINANE; 2H 1,4,2 OXAZAPHOSPHINANE; ALPHA [(2 HYDROXY 1,2 DIPHENYLETHYLAMINO)BENZYL]PHENYLPHOSPHINIC ACID; ALPHA AMINOBENZYLPHENYLPHOSPHINIC ACID; BENZYLPHENYLPHOSPHINIC ACID; HALIDE; PALLADIUM; PHOSPHINE DERIVATIVE; PHOSPHINIC ACID DERIVATIVE; PHOSPHORUS DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; DEPROTECTION REACTION; DRUG SYNTHESIS; METHODOLOGY; PRIORITY JOURNAL;

EID: 20444436010     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.05.007     Document Type: Article

References (39)

1. J. Grembecka, A. Mucha, T. Cierpicki, and P. Kafarski J. Med. Chem. 46 2003 2641 2655
2. K. Maskos, D. Jozic, J.T. Kaiser, R. Huber, and W. Bode J. Mol. Biol. 332 2003 243 256
3. B. Stowasser, K.-H. Budt, L. Jian-Qi, A. Peyman, and D. Ruppert Tetrahedron Lett. 33 1992 6625 6628
4. (d) Stowasser, B.; Li, J. Q.; Peyman, A.; Budt, K. H. US Patent 5663139, 1997. Chem. Abstr. 121, 280877.
5. G.B. Dreyer, S.S. Abdel-Meguid, B. Zhao, K. Murthy, E. Winborne, J.W. Choi, R.L. DesJarlais, M.D. Minnich, J.S. Culp, C. Debouck, T.A. Tomaszek Jr., and T.D. Meek Biochemistry 32 1993 7972 7980
6. (f) Dreyer, G. B. World Patent 9200954, 1992; Chem. Abstr. 116, 236170.
7. (g) Peyman, A.; Stahl, W.; Budt, K.- H.; Ruppert, D.; Schuessler, H.; Wagner, K. US patent 5707979, 1998; Chem. Abstr. 124, 261356.
8. (h) Bolton, G. L.; Padia, J. K.; Trivedi, B. K. US Patent 5208224, 1993; Chem. Abstr. 119, 95833.
9. B. Lejczak, P. Kafarski, and J. Zygmunt Biochemistry 28 1989 3549 3555
10. M. Li, Z. Lin, and M.E. Johnson Bioorg. Med. Chem. Lett. 9 1999 1957 1962
11. Y. Nishizuka Nature 308 1984 693 698
12. V.L. Boyd, M.F. Summers, S.M. Ludeman, W. Ega, G. Zon, and J.B. Regan J. Med. Chem. 30 1987 366 374
13. J. Bergman, H.C. Van der Plas, and M. Simonyi Heterocycles in Bioorganic Chemistry 1991 RSC Cambridge
14. S.Y. Wu, and J.E. Casida Phosphorus, Sulfur, Silicon 102 1995 177
15. C.D. Reddy, M.S. Reddy, and K.D. Berlin Phosphorus, Sulfur, Silicon 102 1995 103
16. B.H. Lipshutz Chem. Rev. 86 1986 795 819
17. H.-J. Cristau, J. Monbrun, M. Tillard, and J.-L. Pirat Tetrahedron Lett. 44 2003 3183 3186
18. (b) Pirat, J.-L.; Monbrun, J.; Virieux, D.; Volle, J.-N.; Tillard, T.; Cristau, H.-J. J. Org. Chem. Submitted for publication.
19. M.C. Chrysselis, E.A. Rekka, and P.N. Kourounakis J. Med. Chem. 43 2000 609 612
20. J.L. Kelley, D.L. Musso, G.E. Boswell, F.E. Soroko, and B.R. Cooper J. Med. Chem. 39 1996 347 349
21. D.L. Musso, and J.L. Kelley Tetrahedron: Asymmetry 8 1995 1841 1844
22. (d) Kelley, J. L.; Musso, D. L.; Boswell, G. E.; Cooper, B. R. Eur. Pat. 426416, 1991; Chem. Abstr. 115, 92281.
23. (e) Morgan, P. F.; Musso, D. L.; Partridge, J. J. World Patent 9937305, 1999; Chem. Abstr. 131, 111445.
24. P.B. Wyatt, C. Villalonga-Barber, and M. Motevalli Tetrahedron Lett. 40 1999 149 152
25. N. Katagiri, M. Yamamoto, T. Iwaoka, and C. Kaneko Chem. Commun. 20 1991 1429 1430
26. K. Afarinkia, H.M. Binch, and I. Forristal Synlett 12 2000 1771 1772
27. R. Hamilton, R.E. Shute, J. Travers, B. Walker, and B.J. Walker Tetrahedron Lett. 21 1994 3597 3600
28. K. Afarinkia, E. De Pascale, and S. Amara Arkivoc vi 2002 205 211
29. V.V. Ragulin Russ. J. Gen. Chem. 71 2001 1823 1824
30. J. Zhou, Y. Qiu, K. Feng, and R. Chen Synthesis 1 1999 40 42
31. Y. Xu, J. Zhang, G. Huang, and H. Guo Tetrahedron Lett. 29 1988 1955 1958
32. Y. Xu, and Z. Li Tetrahedron Lett. 27 1986 3017 3020
33. Y. Xu, H. Wei, J. Zhang, and G. Huang Tetrahedron Lett. 30 1989 949 952
34. H.-J. Cristau, A. Hervé, and D. Virieux Synthesis 14 2003 2216 2220
35. H. Lei, M.S. Stoakes, and A.L. Schwabacher Synthesis 1992 1255 1260
36. Y. Xu, and J. Zhang Chem. Commun. 1986 1606
37. T. Ogawa, N. Usuki, and N. Ono J. Chem. Soc., Perkin Trans. 1 1998 2953 2958
38. F.M. Menger, and J.H. Smith J. Am. Chem. Soc. 1969 4211 4216
39. A. Szabo, Z.M. Jaszay, L. Hegedus, L. Toke, and I. Penehazy Tetrahedron Lett. 44 2003 4603 4606