Phosphinamide-directed ortho metalations: Application to the desymmetrization of the diphenylphosphoryl group

Synlett

Volumn , Issue 4, 2007, Pages 611-614

  Fernández, Ignacio ^a   Burgos, Pascual Oña ^a   Gómez, Gloria Ruiz ^a   Bled, Caroline ^a   García Granda, Santiago ^b   Ortiz, Fernando López ^a  

^a UNIVERSITY OF ALMERÍA   (Spain)

^b UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Diastereoselectivity; Directed metalation; Organotin; ortho lithiation; Phosphinamides

Indexed keywords

AMIDE; DIPHENYLPHOSPHINAMIDE DERIVATIVE; HEMPA; N,N' DIMETHYLPROPYLENE UREA; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CONJUGATION; LITHIATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 33947323909     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-967976     Document Type: Article

References (52)

1. For some recent reviews on the DoM reaction of arenes, see: (a) Snieckus, V. Chem. Rev. 1990, 90, 879.
2. (b) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
3. (c) Mugesh, G.; Singh, H. B. Acc. Chem. Res. 2002, 35, 226.
4. (d) Schlosser, M. Angew. Chem. Int. Ed 2005, 44, 376.
5. (a) Green, L.; Chauder, B.; Snieckus, V. J. Heterocycl. Chem. 1999, 36, 1453.
6. (b) Milburn, R. R.; Snieckus, V. Angew. Chem. Int. Ed. 2004, 43, 888.
7. (c) Macklin, T. K.; Snieckus, V. Org. Lett. 2005, 7, 2519.
8. (d) Nguyen, T.-H.; Castanet, A.-S.; Mortier, J. Org. Lett. 2006, 8, 765.
9. For reviews, see: (a) Wheatley, A. E. Eur. J. Inorg. Chem. 2003, 3291.
10. (b) Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem. Int. Ed. 2004, 43, 2206.
11. See also: (c) Clegg, W.; Dale, S. H.; Hevia, E.; Honeyman, G. W.; Mulvey, R. E. Angew. Chem. Int. Ed. 2006, 45, 2370.
12. (d) Clegg, W.; Dale, S. H.; Harrington, R. W.; Hevia, E.; Honeyman, G. W.; Mulvey, R. E. Angew. Chem. Int. Ed. 2006, 45, 2374.
13. Phosphazenes: (a) Stuckwisch, C. G. J. Org. Chem. 1976, 41, 1173.
14. (b) Steiner, A.; Stalke, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1752.
15. (c) Boubekeur, L.; Ricard, L.; Mézailles, N.; Demange, M.; Auffrant, A.; Le Floch, P. Organometallics 2006, 25, 3091.
16. (d) Phosphorus ylides: Schaub, B.; Jenny, T.; Schlosser, M. Tetrahedron Lett. 1984, 25, 4097.
17. Phosphine oxides: (e) Desponds, O.; Schlosser, M. J. Organomet. Chem. 1996, 507, 257.
18. (f) Ariffin, A.; Blake, A. J.; Li, W.-S.; Simpkins, N. S. Synlett 1997, 1453.
19. (g) Gray, M.; Chapell, B. J.; Felding, J.; Taylor, N. J.; Snieckus, V. Synlett 1998, 422.
20. (h) Phosphine sulfides and thiophosphinamides: Yoshifuji, M.; Ishizuka, T.; Choi, Y. J.; Inamoto, N. Tetrahedron Lett. 1984, 25, 553.
21. (i) Phosphine-borane complexes: Desponds, O.; Huynh, C.; Schlosser, M. Synthesis 1998, 983.
22. (j) Phosphonamides: Dashan, L.; Trippelt, S. Tetrahedron Lett. 1983, 24, 2039.
23. (k) Thiophosphinamides: Craig, D. C.; Roberts, N. K.; Tanswell, J. L. Aust. J. Chem. 1990, 43, 1487.
24. Tsuhji, H.; Komatsu, S.; Kanda, Y.; Umehara, T.; Saeki, T.; Tamao, K. Chem. Lett. 2006, 35, 758.
25. (a) Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Helv. Chim. Acta 1991, 74, 370.
26. (b) Brown, J. M.; Woodward, S. J. Org. Chem. 1991, 56, 6803.
27. (c) Alcock, N. W.; Brown, J. M.; Pearson, M.; Woodward, S. Tetrahedron: Asymmetry 1992, 3, 17.
28. (a) Fernández, I.; López-Ortiz, F.; Tejerina, B.; García-Granda, S. Org. Lett. 2001, 3, 1339.
29. (b) Fernández, I.; López-Ortiz, F.; Menéndez- Velázquez, A.; García-Granda, S. J. Org. Chem. 2002, 67, 3852.
30. (a) Morán Ramallal, A.; López-Ortiz, F.; González, J. Org. Lett. 2004, 6, 2141.
31. (b) Morán Ramallal, A.; Fernández, I.; López-Ortiz, F.; González, J. Chem. Eur. J. 2005, 11, 3022.
32. (a) Fernández, I.; Forcén-Acebal, A.; López-Ortiz, F.; García-Granda, S. J. Org. Chem. 2003, 68, 4472.
33. (b) Fernández, I.; González, J.; López-Ortiz, F. J. Am. Chem. Soc. 2004, 126, 12551.
34. (a) Abatjoglou, A. G.; Eliel, E. L. J. Org. Chem. 1974, 39, 3042.
35. (b) Magnus, P.; Roy, G. Synthesis 1980, 575.
36. (a) Gutmann, V.; Mörtl, G.; Utvary, K. Monatsh. Chem. 1962, 93, 1114.
37. (b) For spectroscopic data of 4, see: Cristau, H.-J.; Jouanin, I.; Taillefer, M. J. Organomet. Chem. 1999, 584, 68.
38. 15
39. The analogous reaction of N,N-dialkylthiophosphinamides produced the quantitative displacement of the amino moiety. See reference 4h.
40. 28NOPSn: C, 57.06; H, 5.83;
41. (a) Puterbaugh, W. H.; Hauser, C. R. J. Org. Chem. 1964, 29, 853.
42. (b) Beak, P.; Brown, R. A. J. Org. Chem. 1979, 44, 4463.
43. (c) Kende, A. S.; Boettger, S. D. J. Org. Chem. 1981, 46, 2799.
44. (d) Epsztajn, J.; Malinowski, Z.; Brzezinki, J. K.; Karzatka, M. Synthesis 2001, 2085.
45. (e) Tois, J.; Koskinen, A. Tetrahedron Lett. 2003, 44, 2093.
46. Both substrates 13 and 14 were synthesized following literature methods: Burns, B.; King, N. P.; Tye, H.; Studley, J. R.; Gamble, M.; Wills, M. J. Chem. Soc., Perkin Trans, 1 1998, 1027.
47. Fernández, I.; Ruiz-Gómez, G.; Alfonso, I.; Iglesias, M. J.; López-Ortiz, F. Chem. Commun. 2005, 5408.
48. The crystal data of 18′ has been deposited in CCDC with number 625923.
49. (a) Nettekoven, U.; Widhalm, M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Mereiter, K.; Lutz, M.; Spek, A. Organometallics 2000, 19, 2299.
50. (b) Vinci, D.; Mateus, N.; Wu, X.; Hancock, F.; Steiner, A.; Xiao, J. Org. Lett. 2006, 8, 215.
51. (c) See also ref. 4e-g.
52. (d) For other diastereoselective deprotonations of ferrocene, see: Metallinos, C.; Snieckus, V. Org. Lett. 2002, 4, 1935; and references therein.