Resolution of chiral (trimethylenemethane) iron (tricarbonyl) complexes

Tetrahedron Asymmetry

Volumn 7, Issue 11, 1996, Pages 3193-3202

  Franck Neumann, Michel ^a   Stöber, Paul ^a,b   Passmore, Guy ^a,c  

^a UNIVERSITÉ LOUIS PASTEUR   (France)

^b Abteilung Klinische Sozialmedizin Berufs und Umweltdermatologie   (Germany)

^c IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

IRON COMPLEX;

ARTICLE; COMPLEX FORMATION; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030575847     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00422-3     Document Type: Article

References (25)

1. (1) R. Grée, Synthesis 1989, 1989, 341-355 and references cited therein.
2. (2) R. W. Baker, S. G. Davies, Tetrahedron: Asymmetry 1993, 4, 1479-1480.
3. (3) A. Efraty, Chem. Rev. 1977, 77, 691-744.
4. (4) A. J. Birch, P. E. Cross, J. Lewis, D. A. White, S. B. Wild, J. Chem. Soc. A 1968, 332-340.
5. (5) M. Franck-Neumann, P. Geoffroy, A. Winling, Synlett 1995, 341-343.
6. (6) K. Ehrlich, G. F. Emerson, J. Am. Chem. Soc. 1972, 94, 2464-2470. cf M.D. Jones, R.D.W. Kemmitt, in Advances in Organometallic Chemistry Vol. 27, 279-309; F.G.A. Stone, R. West (Eds.) Academic Press, San Diego (1987)
7. (6) K. Ehrlich, G. F. Emerson, J. Am. Chem. Soc. 1972, 94, 2464-2470. cf M.D. Jones, R.D.W. Kemmitt, in Advances in Organometallic Chemistry Vol. 27, 279-309; F.G.A. Stone, R. West (Eds.) Academic Press, San Diego (1987)
8. (7) M.-P. Heitz, Thèse de Doctorat es Sciences physiques, Université Louis Pasteur de Strasbourg (1983)
9. (8) M. Franck-Neumann, D. Martina, M.-P. Heitz, Tetrahedron Lett. 1989, 30, 6679-6682.
10. (9) M. Franck-Neumann, A. Kastler, Synlett 1995, 61 -63.
11. f ∼ 0.15), however without any obvious advantage compared to α-methylbenzylamine.
12. f ∼ 0.15), however without any obvious advantage compared to α-methylbenzylamine.
13. f ∼ 0.15), however without any obvious advantage compared to α-methylbenzylamine.
14. (11) B. R. Bonazza, C. P. Lillya, E. S. Magyar, G. Scholes, J. Am. Chem. Soc. 1979, 101, 4100-4106.
15. (12) P. A. Dobosh, P. Lillya, E. S. Magyar, G Scholes,Inorg. Chem. 1980, 19, 228-232.
16. (13) A. Kastler, Thèse de Doctorat de l'Université Louis Pasteur de Strasbourg (1992), cf. M. Franck-Neumann, A. Kastler, P.-J. Colson, Tetrahedron, Lett. 1991, 32, 7051-7054.
17. (13) A. Kastler, Thèse de Doctorat de l'Université Louis Pasteur de Strasbourg (1992), cf. M. Franck-Neumann, A. Kastler, P.-J. Colson, Tetrahedron, Lett. 1991, 32, 7051-7054.
18. (14) N-hydroxysuccinimide esters are well known from peptide synthesis, where they are particularly advantageous (good crystallization properties, high activation, weak racemization). cf. G. Wendlberger, in "Houben-Weyl" Vol. 15/2, pages 111-113 and 149-166, E. Wünsch (ed.), Georg Thieme Verlag, Stuttgart (1974)
19. (15) J. R. K. Boeckman, S. S. Ko, J. Am. Chem. Soc. 1982, 104, 1033-1041.
20. (16) D. Kappes, H. Gerlach, P. Zbinden, M. Dobler, W. A. König, R. Krebber, G. Wenz, Angew. Chem. 1989, 101, 1744-1745; Angew. Chem. Int. Ed. Engl. 1989, 28, 1657-1659.
21. (16) D. Kappes, H. Gerlach, P. Zbinden, M. Dobler, W. A. König, R. Krebber, G. Wenz, Angew. Chem. 1989, 101, 1744-1745; Angew. Chem. Int. Ed. Engl. 1989, 28, 1657-1659.
22. (17) D. Kappes, H. Gerlach, P. Zbinden, M. Dobler, Helv. Chim. Acta 1990, 73, 2136-2146.
23. (18) For metal π-complexes, the absolute configurations (R, S-system) result from the description in terms of single bonds for all metal-ligand interactions.
24. w = 0.039. Further details of the crystal structure may be requested from the Director, Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK, on quoting the full literature citation for the communication.
25. (20) D. L. Flynn, R. E. Zelle, P. A. Grieco, J. Org. Chem. 1983, 48, 2424-2426.