Chemoselective, metal-mediated oxidation of (dienol)iron complexes with N-methylmorpholine N-oxide

Tetrahedron Letters

Volumn 39, Issue 5-6, 1998, Pages 343-346

  Dasgupta, Bireshwar ^a   Donaldson, William A ^a  

^a Marquette University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IRON COMPLEX;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032576804     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10516-0     Document Type: Article

References (33)

1. (1) (a) Donaldson, W. A. in "Comprehensive Organometallic Chemistry II", Abel, E. W.; Stone, F. G. A.; Wilkenson, G. (eds.), Elsevier Science Ltd., Oxford, 1995, Vol. 11, Chpt 6.2;
2. (b) Grée, R.; Lellouche, J. P. in "Advances in Metal-Organic Chemistry", Liebeskind, L. (ed.), JAI Press, Greenwich, CT, 1995, Vol. 4, p. 129-273.
3. (2) (a) Franck-Neurnann, M.; Martina, D.; Heitz, M.P. Tetrahedron Lett. 1982, 23, 3493-6;
4. (b) Monpert, A.; Martelli, J., Grée, R.; Carrié, R. New J. Chem. 1983, 7, 345-6;
5. (c) Boulaajaj, S.; LeGall, T.; Vaultier, M.; Grée, R.; Toupet, L.; Carrié. R. Tetrahedron Lett. 1987, 28, 1761-4;
6. (d) Laabassi, M.; Grée, R. Tetrahedron Lett. 1988, 29,611-4;
7. (e) Donaldson, W.A.; Jin, M.-J. Tetrahedron 1993, 49, 8787-94;
8. (f) LeGall, T.; Lellouche, J.-P.; Beaucourt, J.-P. Tetrahedron Lett. 1989, 30, 6521-4;
9. (g) Nunn, K.; Mosset, P.; Grée, R.; Saalfrank, R.W. Angew. Chem., Int. Ed. Engl. 1988, 27, 1188-9;
10. (h) Gigou, A.; Lellouche, J.-P.; Beaucourt, J.-P.; Toupet, L.; Grée, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 755-7;
11. (i) Gigou, A.; Beaucourt, J.-P.; Lellouche, J.-P.; Grée, R. Tetrahedron Lett. 1991, 32, 635-8;
12. (j) Franck-Neumann, M.; Colson, P.-J. Synlett 1991,891-4;
13. (k) Nunn, K.; Mosset, P.; Grée, R.; Saalfrank, R.W. J. Org. Chem. 1992, 57, 3359-64;
14. (l) Tao, C.; Donaldson, W.A. J. Org. Chem. 1993, 58, 2134-43;
15. (m) Grée, D.M.; Martelli, J.T.; Grée, R.L.; Toupet, L.J. J. Org. Chem. 1995, 60, 2316-7;
16. (n) Laabassi, M.; Grée, R. Tetrahedron Lett. 1989, 30, 6683-6;
17. (o) Benvegnu, T.; Schio, L.; LeFloc'h, Y.; Grée, R. Synlett 1994, 505-6;
18. (p) Prahlad, V.; Donaldson, W.A. Tetrahedron Lett. 1996, 37, 9169-72;
19. (q) Wasicak, J.T.; Craig, R.A.; Henry, R.; Dasgupta, B.; Li, H.; Donaldson, W.A. Tetrahedron 1997, 53, 4185-98;
20. (r) Wada, A.; Hiraishi, S.; Takamura, N.; Date, T.; Aoe, K.; Ito, M. J. Org. Chem. 1997, 62, 4343-8;
21. (s) Roush, W.R.; Wada, C.K. J. Am. Chem. Soc. 1994, 116, 2151-2.
22. (3) Grée, D.M. ; Kermarrec, C.J.M.; Martelli, J.T.; Grée, R.L. J. Org. Chem. 1996, 61, 1918-9.
23. (4) Barrett, A.G.M.; Barton, D.H.R; Johnson, G. J. Chem. Soc., Perkin Trans. I 1978, 1014-7.
24. (5) Adams, C.M.; Cerioni, G.; Hafner, A.; Kalchhauser, H.; von Philipsborn, W.; Prewo, R.; Schwenk, A. Helv. Chim. Acta 1988, 71, 1116.
25. 4 or TPAP, however it has been used to oxidize allylic bromides to the corresponding α,β-unsaturated aldehydes: Griffith, W.P.; Jolliffe, J. M.; Ley, S. V.; Springhorn, K. F.; Tiffin, P. D. Syn. Commun. 1992, 22, 1967-71.
26. (7) Mahler, J. E.; Gibson, D. H.; Pettit, R. J. Am. Chem. Soc. 1963, 85, 3959-63.
27. (8) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504-12; Barton, D. H. R.; Bolvin, J.; Gastiger, M.; Morzycki, J.; Hay-Motherwell, R. S.; Motherwell, W. B.; Ozbalik, N.; Schwartzentruber, K. M. J. Chem. Soc., Perkin Trans. 1 1986, 947-55.
28. (8) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504-12; Barton, D. H. R.; Bolvin, J.; Gastiger, M.; Morzycki, J.; Hay-Motherwell, R. S.; Motherwell, W. B.; Ozbalik, N.; Schwartzentruber, K. M. J. Chem. Soc., Perkin Trans. 1 1986, 947-55.
29. (9) Howell, J. A. S.; Squibb, A. D.; Bell, A. G.; McArdle, P.; Cunningham, D.; Goldschmidt, Z.; Gottlieb, H. E.; Hezroni-Langerman, D.; Grée, R. Organometallics, 1994, 73, 4336-51.
30. (10) Howell, J.A.S.; Palin, M.G.; Jaouen, G.; Top, S.; El Hafa, H.; Cense, J.M. Tetrahedron: Asymm. 1993, 4, 1241-52.
31. (11) Hegedus, L. S. "Transition Metals in the Synthesis of Complex Organic Molecules", University Science Books, Mill Valley, CA, 1994, p. 20.
32. (12) Complex 8 was prepared by NaBH4 reduction of the lactol of (4-hydroxy-5,7-nonadienal)Fe(CO)3.13
33. (13) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829-32.