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Volumn 8, Issue 16, 1997, Pages 2667-2670

New chiral C2-symmetric bis(oxazolinylpyridinyl)dioxolane ligands for asymmetric catalysis: Palladium catalysed allylic substitution

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; LIGAND; PALLADIUM COMPLEX; PYRIDINE DERIVATIVE;

EID: 0030928644     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00318-2     Document Type: Article
Times cited : (56)

References (25)
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    • Chelucci, G.; Berta, D.; Saba, A. Tetrahedron, 1997, 53, 3843. Chelucci, G.; Marchetti, M.; Sechi, B. J. Organomet. Chem., 1997, in press. Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, C.; Marchetti, M. Tetrahedron: Asymmetry, 1996, 7, 885. Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry, 1996, 7, 965.
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    • in press.
    • Chelucci, G.; Berta, D.; Saba, A. Tetrahedron, 1997, 53, 3843. Chelucci, G.; Marchetti, M.; Sechi, B. J. Organomet. Chem., 1997, in press. Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, C.; Marchetti, M. Tetrahedron: Asymmetry, 1996, 7, 885. Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry, 1996, 7, 965.
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    • Chelucci, G.1    Marchetti, M.2    Sechi, B.3
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    • Chelucci, G.; Berta, D.; Saba, A. Tetrahedron, 1997, 53, 3843. Chelucci, G.; Marchetti, M.; Sechi, B. J. Organomet. Chem., 1997, in press. Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, C.; Marchetti, M. Tetrahedron: Asymmetry, 1996, 7, 885. Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry, 1996, 7, 965.
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    • Chelucci, G.1    Cabras, M.A.2    Botteghi, C.3    Basoli, C.4    Marchetti, M.5
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    • Chelucci, G.; Berta, D.; Saba, A. Tetrahedron, 1997, 53, 3843. Chelucci, G.; Marchetti, M.; Sechi, B. J. Organomet. Chem., 1997, in press. Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, C.; Marchetti, M. Tetrahedron: Asymmetry, 1996, 7, 885. Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry, 1996, 7, 965.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 965
    • Chelucci, G.1    Cabras, M.A.2
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    • Nishiyama, H.; Yamaguchi, S.; Park, S.-B.; Itoh, K. Tetrahedron: Asymmetry, 1993, 4, 143. For recent applications of oxazolinylpyridines as ligands for asymmetric catalytic reactions., see: Davies, I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 38, 1145. DattaGupta, A.; Singh, V. Tetrahedron Lett., 1996, 57, 2633. Park, S.-B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Brunner, H.; Henrichs, C. Tetrahedron: Asymmetry, 1995, 6, 653 and references therein.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 143
    • Nishiyama, H.1    Yamaguchi, S.2    Park, S.-B.3    Itoh, K.4
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    • 0031575566 scopus 로고    scopus 로고
    • Nishiyama, H.; Yamaguchi, S.; Park, S.-B.; Itoh, K. Tetrahedron: Asymmetry, 1993, 4, 143. For recent applications of oxazolinylpyridines as ligands for asymmetric catalytic reactions., see: Davies, I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 38, 1145. DattaGupta, A.; Singh, V. Tetrahedron Lett., 1996, 57, 2633. Park, S.-B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Brunner, H.; Henrichs, C. Tetrahedron: Asymmetry, 1995, 6, 653 and references therein.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1145
    • Davies, I.W.1    Gerena, L.2    Cai, D.3    Larsen, R.D.4    Verhoeven, T.R.5    Reider, P.J.6
  • 9
    • 0029965482 scopus 로고    scopus 로고
    • Nishiyama, H.; Yamaguchi, S.; Park, S.-B.; Itoh, K. Tetrahedron: Asymmetry, 1993, 4, 143. For recent applications of oxazolinylpyridines as ligands for asymmetric catalytic reactions., see: Davies, I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 38, 1145. DattaGupta, A.; Singh, V. Tetrahedron Lett., 1996, 57, 2633. Park, S.-B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Brunner, H.; Henrichs, C. Tetrahedron: Asymmetry, 1995, 6, 653 and references therein.
    • (1996) Tetrahedron Lett. , vol.57 , pp. 2633
    • DattaGupta, A.1    Singh, V.2
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    • Nishiyama, H.; Yamaguchi, S.; Park, S.-B.; Itoh, K. Tetrahedron: Asymmetry, 1993, 4, 143. For recent applications of oxazolinylpyridines as ligands for asymmetric catalytic reactions., see: Davies, I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 38, 1145. DattaGupta, A.; Singh, V. Tetrahedron Lett., 1996, 57, 2633. Park, S.-B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Brunner, H.; Henrichs, C. Tetrahedron: Asymmetry, 1995, 6, 653 and references therein.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 2487
    • Park, S.-B.1    Murata, K.2    Matsumoto, H.3    Nishiyama, H.4
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    • references therein
    • Nishiyama, H.; Yamaguchi, S.; Park, S.-B.; Itoh, K. Tetrahedron: Asymmetry, 1993, 4, 143. For recent applications of oxazolinylpyridines as ligands for asymmetric catalytic reactions., see: Davies, I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 38, 1145. DattaGupta, A.; Singh, V. Tetrahedron Lett., 1996, 57, 2633. Park, S.-B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Brunner, H.; Henrichs, C. Tetrahedron: Asymmetry, 1995, 6, 653 and references therein.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 653
    • Brunner, H.1    Henrichs, C.2
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    • During the drafting of this paper a study on the application of chiral oxazolinylpyridines as ligands for enantioselective palladium catalysed allylic substitutions was reported: Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. Our related study will appear shortly: Chelucci, G.; Medici, S.; Saba, A.; paper submitted for publication.
    • (1997) J. Org. Chem. , vol.62 , pp. 1604
    • Nordström, K.1    Macedo, E.2    Moberg, C.3
  • 13
    • 0001542678 scopus 로고    scopus 로고
    • paper submitted for publication
    • During the drafting of this paper a study on the application of chiral oxazolinylpyridines as ligands for enantioselective palladium catalysed allylic substitutions was reported: Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. Our related study will appear shortly: Chelucci, G.; Medici, S.; Saba, A.; paper submitted for publication.
    • Chelucci, G.1    Medici, S.2    Saba, A.3
  • 17
    • 0343776297 scopus 로고    scopus 로고
    • note
    • 3) δ 8.00 (d, 1H), 7.84-7.71 (m, 2H), 5.29 (s, 1H), 4.11 (s, 2H), 1.66 (s, 3H), 1.33 (s, 6H).
  • 19
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    • Trost, M. B.; Van Vranken, D. L. Chem. Rev., 1996, 96, 395. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547. Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron: Asymmetry, 1995, 6, 2535, and references therein.
    • (1996) Chem. Rev. , vol.96 , pp. 395
    • Trost, M.B.1    Van Vranken, D.L.2
  • 20
    • 6844254916 scopus 로고    scopus 로고
    • Trost, M. B.; Van Vranken, D. L. Chem. Rev., 1996, 96, 395. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547. Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron: Asymmetry, 1995, 6, 2535, and references therein.
    • (1993) Angew. Chem. , vol.105 , pp. 576
    • Reiser, O.1
  • 21
    • 33748245787 scopus 로고
    • Trost, M. B.; Van Vranken, D. L. Chem. Rev., 1996, 96, 395. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547. Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron: Asymmetry, 1995, 6, 2535, and references therein.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 547
  • 22
    • 6844254916 scopus 로고    scopus 로고
    • Ed. Ojima, VCH, Weinheim
    • Trost, M. B.; Van Vranken, D. L. Chem. Rev., 1996, 96, 395. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547. Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron: Asymmetry, 1995, 6, 2535, and references therein.
    • (1993) Catalytic Asymmetric Synthesis
    • Hayashi, T.1
  • 23
    • 0026722772 scopus 로고
    • Trost, M. B.; Van Vranken, D. L. Chem. Rev., 1996, 96, 395. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547. Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron: Asymmetry, 1995, 6, 2535, and references therein.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 1089
    • Frost, C.G.1    Howarth, J.2    Williams, J.M.J.3
  • 24
    • 0028882941 scopus 로고
    • references therein
    • Trost, M. B.; Van Vranken, D. L. Chem. Rev., 1996, 96, 395. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547. Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron: Asymmetry, 1995, 6, 2535, and references therein.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 2535
    • Dawson, G.J.1    Williams, J.M.J.2    Coote, S.J.3


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