η4 to η5 stereocontrolled reactivation of exocyclic triene iron complexes

Tetrahedron Letters

Volumn 39, Issue 41, 1998, Pages 7603-7606

  Anson, Christopher E ^a   Hudson, Richard D A ^a   Osborne, Simon A ^b   Smyth, Donald G ^a   Stephenson, G Richard ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^b Parke Davis Neurosci Res Center   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EXOCYCLIC DOUBLE BOND; TRIENTINE;

ARTICLE; CHIRALITY; COMPLEX FORMATION; DRUG SYNTHESIS; IRON METABOLISM; NONHUMAN; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0032497717     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01653-0     Document Type: Article

References (16)

1. 1. For example: Knölker, H. J.; Fröhner, W. Tetrahedron Lett., 1996, 37, 9183; Stephenson, G. R.; Finch, H.; Owen, D. A.; Swanson, S. Tetrahedron, 1993, 49, 5649; Pearson, A. J.; O'Brien, M. K. J. Org. Chem., 1989, 54, 4663; Birch, A. J.; Kelly, L. F.; Bandara, B. M. R. J. Org. Chem., 1984, 49, 2496.
2. 1. For example: Knölker, H. J.; Fröhner, W. Tetrahedron Lett., 1996, 37, 9183; Stephenson, G. R.; Finch, H.; Owen, D. A.; Swanson, S. Tetrahedron, 1993, 49, 5649; Pearson, A. J.; O'Brien, M. K. J. Org. Chem., 1989, 54, 4663; Birch, A. J.; Kelly, L. F.; Bandara, B. M. R. J. Org. Chem., 1984, 49, 2496.
3. 1. For example: Knölker, H. J.; Fröhner, W. Tetrahedron Lett., 1996, 37, 9183; Stephenson, G. R.; Finch, H.; Owen, D. A.; Swanson, S. Tetrahedron, 1993, 49, 5649; Pearson, A. J.; O'Brien, M. K. J. Org. Chem., 1989, 54, 4663; Birch, A. J.; Kelly, L. F.; Bandara, B. M. R. J. Org. Chem., 1984, 49, 2496.
4. 1. For example: Knölker, H. J.; Fröhner, W. Tetrahedron Lett., 1996, 37, 9183; Stephenson, G. R.; Finch, H.; Owen, D. A.; Swanson, S. Tetrahedron, 1993, 49, 5649; Pearson, A. J.; O'Brien, M. K. J. Org. Chem., 1989, 54, 4663; Birch, A. J.; Kelly, L. F.; Bandara, B. M. R. J. Org. Chem., 1984, 49, 2496.
5. 2. Birch, A. J.; Bandara, B. M. R.; Chaimberlain, K.; Chauncy, B.; Dahler, P.; Day, A. I.; Jenkins, I. D.; Kelly, L. F.; Khor, T.-C.; Kretschmer, G.; Liepa, A. J.; Narular, A. S.; Raverty, W. D.; Rizzardo, E.; Sell, C.; Stephenson, G. R.; Thompson, D. J.; Williamson, D. H. Tetrahedron, 1981, 37, Suppl. 1, 289.
6. 3. The working ligand is defined as the portion of the complex which is destined to be stoichiometrically incorporated into the organic target structure: Stephenson, G. R. in Advanced Asymmetric Synthesis, Blackie: London, 1996, pg 319.
7. 4. Fischer, E. O.; Fischer, R. D. Angew. Chem., 1960, 72, 919.
8. 5. Birch, A. J.; Kelly, L. F.; Thompson, D. J. J. Organomet. Chem., 1985, 286, 37.
9. 6. Birch, A. J.; Williamson, D. H. J. Chem. Soc., Perkin Trans. 1, 1973, 1892.
10. 7. Howell, J. A. S.; Thomas, M. J.; J. Organomet. Chem., 1983, 247, C21.
11. 8. Birch, A. J.; Chaimberlain, K.; Haas, M. A.; Thompson, D. J. J. Chem. Soc., Perkin Trans. 1, 1973, 1882.
12. 9. Anson, C. E.; Attwood, M. R.; Raynham, T. M.; Smyth, D. G.; Stephenson, G. R. Tetrahedron Lett., 1997, 38, 305.
13. 10. Hudson R. D. A.; Osborne, S. A.; Roberts, E.; Stephenson, G. R. Tetrahedron Lett., 1997, 37, 9009.
14. 11. Stephenson, G. R.; Voyle, M.; Williams, S. Tetrahedron Lett., 1990, 31, 3979.
15. -1. The solution was poured into diethyl ether and a dense yellow precipitate formed. This was collected by filtration and redissolved in a minimum of acetone. Reprecipitation by addition to diethyl ether afforded the cyclohexadienyliron compound as a yellow solid.
16. 1 (F > 4σ(F)) = 0.0426.