More efficient iterative uses of tricarbonyliron complexes are possible by diastereoselective formation of η5-Cyclohexadienyl complexes

Tetrahedron Letters

Volumn 38, Issue 4, 1997, Pages 505-508

  Anson, Christopher E ^a   Attwood, Michael R ^b   Raynham, Tony M ^b   Smyth, Donald G ^a   Stephenson, G Richard ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^b ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

IRON COMPLEX;

ARTICLE; CRYSTALLOGRAPHY; DRUG SYNTHESIS; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0031033877     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02360-X     Document Type: Article

References (25)

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2. Reviews of stoichiometric transition metals in organic synthesis: Pearson, A.J. Pure Appl. Chem. 1983, 55, 1767-1779; Grée, R. Synthesis 1989, 341-355; Pearson, A.J. Synlett 1990, 10-19; Stephenson, G. R.; Astley, S. T.; Palotai, I. M.; Howard, P. W.; Owen, D. A.; Williams, S. Regiocontrolled Application of Transition Metal π-complexes, in K. H. Dötz and R. W. Hoffmann (Eds.): Organic Synthesis via Organometallics, Vieweg, Braunschweig 1991,169-185; Knölker, H.J. Synlett 1992, 371-387.
3. Reviews of stoichiometric transition metals in organic synthesis: Pearson, A.J. Pure Appl. Chem. 1983, 55, 1767-1779; Grée, R. Synthesis 1989, 341-355; Pearson, A.J. Synlett 1990, 10-19; Stephenson, G. R.; Astley, S. T.; Palotai, I. M.; Howard, P. W.; Owen, D. A.; Williams, S. Regiocontrolled Application of Transition Metal π-complexes, in K. H. Dötz and R. W. Hoffmann (Eds.): Organic Synthesis via Organometallics, Vieweg, Braunschweig 1991,169-185; Knölker, H.J. Synlett 1992, 371-387.
4. Reviews of stoichiometric transition metals in organic synthesis: Pearson, A.J. Pure Appl. Chem. 1983, 55, 1767-1779; Grée, R. Synthesis 1989, 341-355; Pearson, A.J. Synlett 1990, 10-19; Stephenson, G. R.; Astley, S. T.; Palotai, I. M.; Howard, P. W.; Owen, D. A.; Williams, S. Regiocontrolled Application of Transition Metal π-complexes, in K. H. Dötz and R. W. Hoffmann (Eds.): Organic Synthesis via Organometallics, Vieweg, Braunschweig 1991,169-185; Knölker, H.J. Synlett 1992, 371-387.
5. Reviews of stoichiometric transition metals in organic synthesis: Pearson, A.J. Pure Appl. Chem. 1983, 55, 1767-1779; Grée, R. Synthesis 1989, 341-355; Pearson, A.J. Synlett 1990, 10-19; Stephenson, G. R.; Astley, S. T.; Palotai, I. M.; Howard, P. W.; Owen, D. A.; Williams, S. Regiocontrolled Application of Transition Metal π-complexes, in K. H. Dötz and R. W. Hoffmann (Eds.): Organic Synthesis via Organometallics, Vieweg, Braunschweig 1991,169-185; Knölker, H.J. Synlett 1992, 371-387.
6. Stephenson, G. R.; Alexander, R. P.; Morley, C.; Howard, P.W. Phil. Trans. R. Soc. Lond. A 1988, 326, 545; Stephenson, G. R. Organometallic Chemistry. Part (1) The Transition Elements. Annual Reports of The Chemical Society 1993, Section B, Organic Chemistry. (Published 1994), 90, 217-267.
7. Stephenson, G. R.; Alexander, R. P.; Morley, C.; Howard, P.W. Phil. Trans. R. Soc. Lond. A 1988, 326, 545; Stephenson, G. R. Organometallic Chemistry. Part (1) The Transition Elements. Annual Reports of The Chemical Society 1993, Section B, Organic Chemistry. (Published 1994), 90, 217-267.
8. For examples of linear bond-forming sequences, see: (a) Chao, K. H.; Faller, J. W.; Murray, H. H. ; White, D. L. Organometallics 1983, 2, 400;
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11. For examples of iterative syntheses, see: (a) Pearson, A. J.; Lai, Y.-S.; Lu, Wenyuan; Pinkerton, A. L. J. Org. Chem. 1989, 54, 3882 (tylosin)
12. (b) Stephenson, G. R.; Finch, H.; Owen, D. A.; Swanson, S. Tetrahedron 1993, 49, 5649 (O-methyljoubertiamine);
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16. Alexander, R. P.; Stephenson, G. R. J. Chem. Soc., Dalton Trans. 1987, 885; Stephenson, G. R. J. Chem. Soc., Perkin Trans. 1. 1982, 2449; Alexander, I. J.; Hales, N. J.; Stephenson, G.R. J. Organometal. Chem. 1993, 453, 111; Randall, G. P.; Stephenson, G. R.; Chrystal, E. J. T. J. Organomet. Chem. 1988, 353, C47-C50.
17. Alexander, R. P.; Stephenson, G. R. J. Chem. Soc., Dalton Trans. 1987, 885; Stephenson, G. R. J. Chem. Soc., Perkin Trans. 1. 1982, 2449; Alexander, I. J.; Hales, N. J.; Stephenson, G.R. J. Organometal. Chem. 1993, 453, 111; Randall, G. P.; Stephenson, G. R.; Chrystal, E. J. T. J. Organomet. Chem. 1988, 353, C47-C50.
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21. (b) Franck-Neumann, M. in Organometallics in Organic Synthesis, de Meijere, A.; Tom-Dieck, H. (Eds.). Springer-Verlag, Berlin, 1987, 247-264.
22. Jablonski, C. R.; Sorenson, T. S. Can. J. Chem. 1974, 52, 2085.
23. For definitions of the stereochemical descriptors ψ-exo and ψ-endo and examples of their use see: Hill, E. A.; Richards, J. H. J. Chem. Soc. 1961, 83, 3840; Kühn, D. E.; Lillya, C. P. J. Am. Chem. Soc. 1972, 94, 1682; and ref 8 a.
24. For definitions of the stereochemical descriptors ψ-exo and ψ-endo and examples of their use see: Hill, E. A.; Richards, J. H. J. Chem. Soc. 1961, 83, 3840; Kühn, D. E.; Lillya, C. P. J. Am. Chem. Soc. 1972, 94, 1682; and ref 8 a.
25. Relative stereochemistry has not been determined. The product 9 was recrystallised from dichloromethane / hexane but the crystals (m.pt. 83-86 °C) proved unsuitable for X-ray diffraction.