A novel P-chirogenic phosphine ligand, (S,S)-1,2-bis-[(ferrocenyl)methylphosphino]ethane: Synthesis and use in rhodium-catalyzed asymmetric hydrogenation and palladium-catalyzed asymmetric allylic alkylation

Tetrahedron Asymmetry

Volumn 14, Issue 15, 2003, Pages 2171-2175

  Oohara, Nobuhiko ^a   Katagiri, Kosuke ^b   Imamoto, Tsuneo ^b  

^a Nippon Chemiphar Co Ltd   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BIS[(FERRONYL)METHYLPHOSPHINO]ETHANE; ACETIC ACID DERIVATIVE; ALKANE DERIVATIVE; AMINO ACID DERIVATIVE; BORANE DERIVATIVE; ETHANE; PALLADIUM; PHOSPHINE; RHODIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; HYDROGENATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0042699953     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00439-7     Document Type: Article

References (33)

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25. 2 resulted in sluggish reaction providing very low enantioselectivity.
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28. For representative reviews, see: (a) Trost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089; (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 1993; pp. 325-365; (c) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395; (d) Trost, B. M.; Lee, C. in Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 593-649; (e) Pflatz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N.; Pflatz, A.; Yamamoto, H., Eds; Springer: Berlin, pp. 833-884.
29. For representative reviews, see: (a) Trost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089; (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 1993; pp. 325-365; (c) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395; (d) Trost, B. M.; Lee, C. in Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 593-649; (e) Pflatz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N.; Pflatz, A.; Yamamoto, H., Eds; Springer: Berlin, pp. 833-884.
30. For representative reviews, see: (a) Trost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089; (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 1993; pp. 325-365; (c) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395; (d) Trost, B. M.; Lee, C. in Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 593-649; (e) Pflatz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N.; Pflatz, A.; Yamamoto, H., Eds; Springer: Berlin, pp. 833-884.
31. For representative reviews, see: (a) Trost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089; (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 1993; pp. 325-365; (c) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395; (d) Trost, B. M.; Lee, C. in Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 593-649; (e) Pflatz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N.; Pflatz, A.; Yamamoto, H., Eds; Springer: Berlin, pp. 833-884.
32. For representative reviews, see: (a) Trost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089; (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 1993; pp. 325-365; (c) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395; (d) Trost, B. M.; Lee, C. in Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 593-649; (e) Pflatz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N.; Pflatz, A.; Yamamoto, H., Eds; Springer: Berlin, pp. 833-884.
33. CCDC 212697 for compound 3 and CCDC 212698 for compound 1 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk).