Preparation of Optically Active α-Amino[3]ferrocenophanes - Building Blocks for Chelate Ligands in Asymmetric Catalysis

European Journal of Inorganic Chemistry

Volumn , Issue 19, 2003, Pages 3590-3600

  Liptau, Patrick ^a   Tebben, Ludger ^a   Kehr, Gerald ^a   Wibbeling, Birgit ^a   Fröhlich, Roland ^a   Erker, Gerhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Chelate ligands; Ferrocenes; Ferrocenophanes

Indexed keywords

CATALYSIS; CHELATION; CHLORINE COMPOUNDS; CRYSTALLINE MATERIALS; ENANTIOMERS; HYDROGENATION; IRON COMPOUNDS; LIGANDS; LIQUID CHROMATOGRAPHY; ORGANOMETALLICS; TITANIUM COMPOUNDS;

ASYMMETRIC CATALYSIS; BUILDING BLOCKES; CATALYTIC HYDROGENATION; CHELATE LIGANDS; DIASTEREOMERIC; DIMETHYLAMINES; FERROCENES; FERROCENOPHANES; OPTICALLY ACTIVE; SALT FORMATION;

AMINES;

ALPHA AMINO[3]FERROCENOPHANE DERIVATIVE; AMINE; CHELATE; DIACETYLFERROCENE; DIMETHYLAMINE; FERROCENE DERIVATIVE; LIGAND; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHROMATOGRAPHY; ENANTIOMER; HYDROGENATION;

EID: 0142245677     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200300152     Document Type: Article

References (53)

1. A. Togni, T. Hayashi (Eds.), Ferrocenes: Homogenous Catalysis, Organic Synthesis, Materials Science, VCH, Weinheim, 1995.
2. [2a] Josiphos: A. Togni, C. Breutel, A. Schnyder, F. Spindler, H. Landert, A. Tijani, J. Am. Chem. Soc. 1994, 116, 4062-4066.
3. [2b] Walphos: T. Sturm, W. Weissensteiner, F. Spindler, Adv. Synth. Catal. 2003, 345, 160-164.
4. [3a] G. Tainturier, K. Chhor y Sok, B. Gautheron, C. R. Acad Sci. Paris C 1973, 1269-1270.
5. [3b] K. Chhor y Sok, G. Tainturier, B. Gautheron, Tetrahedron Lett. 1974, 25, 2207-2208.
6. [3c] K. Chhor y Sok, G. Tainturier, B. Gautheron, J. Organomet. Chem. 1977, 132, 173-189.
7. [4a] A. Mernyi, C. Kratky, W. Weissensteiner, M. Widhalm, J. Organomet. Chem. 1996, 508, 209-218.
8. [4b] F. Gómez-de la Torre, F. A. Jalón, A. López-Agenjo, B. R. Manzano, A. Rodríguez, T. Sturm, W. Weissensteiner, M. Martinez-Ripoll, Organometallics 1998, 17, 4634-4644.
9. [4c] F. A. Jalón, A. López-Agenjo, B. R. Manzano, M. Moreno-Lara, A. Rodriguez, T. Sturm, W. Weissensteiner, J. Chem. Soc., Dalton Trans. 1999, 4031-4039.
10. [4d] T. Sturm, W. Weissensteiner, K. Mereiter, T. Kégl, G. Jeges, G. Petölz, L. Kollár, J. Organomet. Chem. 2000, 595, 93-101.
11. [4e] E. M. Caynela, L. Xiao, T. Sturm, B. R. Manzano, F. A. Jalón, W. Weissensteiner, Tetrahedron: Asymmetry 2000, 11, 861-869.
12. [4f] B. R. Manzano, F. A. Jalón, F. Gómez-De la Torre, A. M. López-Agenjo, A. M. Rodríguez, K. Mereiter, W. Weissensteiner, T. Sturm, Organometallics 2002, 21, 789-802.
13. [4g] T. Sturm, W. Weissensteiner, F. Spindler, K. Mereiter, A. M. López-Agenjo, B. R. Manzano, F. A. Jalón, Organometallics 2002, 21, 1766-1774.
14. M. Weißenbach, T. Sturm, K. Kalchhauser, C. Kratky, W. Weissensteiner, Monatsh. Chem. 2002, 133, 991-1009.
15. [6a] M. Rosenblum, R. B. Woodward, J. Am. Chem. Soc. 1958, 80, 5443-5449.
16. [6b] A. N. Nesmeyanov, E. V. Leonova, N. S. Kochetkova, A. I. Malkova, J. Organomet. Chem. 1975, 96, 271-274.
17. W. A. White, H. Weingarten, J. Org. Chem. 1967, 32, 213-214.
18. [8a] S. Knüppel, R. Fröhlich, G. Erker, J. Organomet. Chem. 1999, 586, 218-222.
19. [8b] S. Knüppel, R. Fröhlich, G. Erker, J. Organomet. Chem. 2000, 595, 308-312.
20. [9a] S. Knüppel, G. Erker, R. Fröhlich, Angew. Chem. 1999, 111, 2048-2051; Angew. Chem. Int. Ed. 1999, 38, 1923-1926.
21. [9a] S. Knüppel, G. Erker, R. Fröhlich, Angew. Chem. 1999, 111, 2048-2051; Angew. Chem. Int. Ed. 1999, 38, 1923-1926.
22. [9b] S.-D. Bai, X.-H. Wei, J.-P. Guo, D.-S. Liu, Z.-Y. Zhou, Angew. Chem. 1999, 111, 2051-2054; Angew. Chem. Int. Ed. 1999, 38, 1926-1928.
23. [9b] S.-D. Bai, X.-H. Wei, J.-P. Guo, D.-S. Liu, Z.-Y. Zhou, Angew. Chem. 1999, 111, 2051-2054; Angew. Chem. Int. Ed. 1999, 38, 1926-1928.
24. P. Liptau, S. Knüppel, G. Kehr, O. Kataeva, R. Fröhlich, G. Erker, J. Organomet. Chem. 2001, 637, 621-630.
25. P. Liptau, T. Seki, G. Kehr, A. Abele, R. Fröhlich, G. Erker, S. Grimme, Organometallics 2003, 22, 2226-2232.
26. [12a] E. Drent, P. H. M. Budzelaar, Chem. Rev. 1996, 96, 663-681.
27. [12b] C. Bianchini, A. Meli, Coord. Chem. Rev. 2002, 225, 35-66.
28. L. A. Paquette, J. Tae, J. Org. Chem. 1998, 63, 2022-2030.
29. K. L. Brown, L. Damm, J. Dunitz, A. Eschenmoser, R. Hobi, C. Kratky, Helv. Chim. Acta 1978, 61, 3108-3135.
30. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Open, J. Chem. Soc., Perkin Trans. 2. 1987, S1-S19.
31. [16a] M. Reetz, M. W. Drewes, A. Schmitz, Angew. Chem. 1987, 99, 1186-1187; Angew. Chem. Int. Ed. Engl. 1987, 26, 1141.
32. [16a] M. Reetz, M. W. Drewes, A. Schmitz, Angew. Chem. 1987, 99, 1186-1187; Angew. Chem. Int. Ed. Engl. 1987, 26, 1141.
33. [16b] W. H. Hartung, R. Simonoff, Org. React. 1953, 7, 263.
34. [16c] J.-L. Vasse, V. Levacher, J. Bourguignon, G. Dupas, Tetrahedron: Asymmetry 2002, 13, 227-232.
35. K. Schlögl, M. Fried, Monatsh. Chem. 1964, 95, 558-575.
36. [18a] D. Marquarding, H. Klusacek, G. Gokel, P. Hoffmann, I. Ugi, J. Am. Chem. Soc. 1970, 92, 5389-5393.
37. [18b] G. Gokel, D. Marquarding, I. Ugi, J. Org. Chem. 1972, 37, 3052-3058.
38. [18c] T. Hayashi, T. Mise, M. Fukushima, M. Kagotani, N. Nagashima, Y. Hamada, A. Matsumoto, S. Kawakami, M. Konishi, K. Yamamoto, M. Kumada, Bull. Chem. Soc. Jpn. 1980, 53, 1138-1151.
39. [18d] C. Ganter, T. Wagner, Chem. Ber 1995, 128, 1157-1161.
40. [19a] For related (fulvene)metal-type structures, see e.g.: M. Watanabe, I. Motoyama, T. Takayama, J. Organomet. Chem. 1996, 524, 9-18.
41. [19b] See also: V. Kupfer, U. Thewalt, I. Tišlerová, P. Štepnicka, R. Gyepes, J. Kubišta, M. Horácek, K. Mach, J. Organomet. Chem. 2001, 620, 39-50.
42. [20a] A. Togni, R. Häusle, Synlett 1990, 633-535.
43. [20b] A. Togni, G. Rihs, R. E. Blumer, Organometallics 1992, 11, 613-621.
44. [21a] C. Gambs, S. Chaloupka, G. Consiglio, A. Togni, Angew. Chem. 2000, 112, 2602-2604; Angew. Chem. Int. Ed. 2000, 39, 2486-2488.
45. [21a] C. Gambs, S. Chaloupka, G. Consiglio, A. Togni, Angew. Chem. 2000, 112, 2602-2604; Angew. Chem. Int. Ed. 2000, 39, 2486-2488.
46. [21b] C. Gambs, G. Consiglio, A. Togni, Helv. Chim. Acta 2001, 84, 3105-3126.
47. S. Braun, H.-O. Kalinowski, S. Berger, 150 and More Basic NMR Experiments, Wiley-VCH, Weinheim, 1995.
48. Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326.
49. R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426
50. R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426
51. SHELXS-97: G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467-473
52. SHELXL-97: G. M. Sheldrick, Universität Göttingen, 1997.
53. SCHAKAL: E. Keller, Universität Freiburg, 1997.