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Volumn 8, Issue 19, 1997, Pages 3183-3184

Chiral oxazolinylpyridines as ligands for enantioselective palladium catalysed allylic substitution

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 OXAZOLINYL)PYRIDINE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030832186     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00425-4     Document Type: Article
Times cited : (49)

References (17)
  • 3
    • 0001542678 scopus 로고    scopus 로고
    • During the drafting of this paper a study on the use of chiral oxazolinylpyridines as ligands for the alkylation of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate has been reported. However, this study was centred on the use of oxazolinylpyridines bearing two stereocentres, one on the oxazoline ring and the other on the carbon bonded to the 6-position of the pyridine ring: Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. For recent applications of oxazolinylpyridines, see: Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 35, 1145. DattaGupta, A.; Singh, V. Tetrahedron Lett., 1996, 37, 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) J. Org. Chem. , vol.62 , pp. 1604
    • Nordström, K.1    Macedo, E.2    Moberg, C.3
  • 4
    • 0031575566 scopus 로고    scopus 로고
    • During the drafting of this paper a study on the use of chiral oxazolinylpyridines as ligands for the alkylation of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate has been reported. However, this study was centred on the use of oxazolinylpyridines bearing two stereocentres, one on the oxazoline ring and the other on the carbon bonded to the 6-position of the pyridine ring: Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. For recent applications of oxazolinylpyridines, see: Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 35, 1145. DattaGupta, A.; Singh, V. Tetrahedron Lett., 1996, 37, 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.35 , pp. 1145
    • Davies, I.W.1    Gerena, L.2    Cai, D.3    Larsen, R.D.4    Verhoeven, T.R.5    Reider, P.J.6
  • 5
    • 0029965482 scopus 로고    scopus 로고
    • During the drafting of this paper a study on the use of chiral oxazolinylpyridines as ligands for the alkylation of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate has been reported. However, this study was centred on the use of oxazolinylpyridines bearing two stereocentres, one on the oxazoline ring and the other on the carbon bonded to the 6-position of the pyridine ring: Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. For recent applications of oxazolinylpyridines, see: Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 35, 1145. DattaGupta, A.; Singh, V. Tetrahedron Lett., 1996, 37, 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.37 , pp. 2633
    • Dattagupta, A.1    Singh, V.2
  • 6
    • 0028861083 scopus 로고
    • During the drafting of this paper a study on the use of chiral oxazolinylpyridines as ligands for the alkylation of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate has been reported. However, this study was centred on the use of oxazolinylpyridines bearing two stereocentres, one on the oxazoline ring and the other on the carbon bonded to the 6-position of the pyridine ring: Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. For recent applications of oxazolinylpyridines, see: Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 35, 1145. DattaGupta, A.; Singh, V. Tetrahedron Lett., 1996, 37, 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
  • 7
    • 0028951053 scopus 로고
    • and references therein
    • During the drafting of this paper a study on the use of chiral oxazolinylpyridines as ligands for the alkylation of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate has been reported. However, this study was centred on the use of oxazolinylpyridines bearing two stereocentres, one on the oxazoline ring and the other on the carbon bonded to the 6-position of the pyridine ring: Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. For recent applications of oxazolinylpyridines, see: Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 35, 1145. DattaGupta, A.; Singh, V. Tetrahedron Lett., 1996, 37, 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
  • 10
    • 6844254916 scopus 로고    scopus 로고
    • For reviews: Trost, M. B.; Van Vranken, D. L. Chem. Rev., 1996, 96, 395. 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.
    • (1996) Chem. Rev. , vol.96 , pp. 395
    • Trost, M.B.1    Van Vranken, D.L.2
  • 11
    • 6844254916 scopus 로고    scopus 로고
    • Ed. Ojima, VCH, Weinheim
    • For reviews: Trost, M. B.; Van Vranken, D. L. Chem. Rev., 1996, 96, 395. 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.
    • (1993) Catalytic Asymmetric Synthesis
    • Hayashi, T.1
  • 12
    • 0026722772 scopus 로고
    • For reviews: Trost, M. B.; Van Vranken, D. L. Chem. Rev., 1996, 96, 395. 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.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 1089
    • Frost, C.G.1    Howarth, J.2    Williams, J.M.J.3
  • 14
    • 0342471124 scopus 로고    scopus 로고
    • Moberg and co-workers used the oxazolinylpyridine 2b in the same reaction as a reference ligand. Their results were very similar to ours. See Nordström et al. 3
    • Moberg and co-workers used the oxazolinylpyridine 2b in the same reaction as a reference ligand. Their results were very similar to ours. See Nordström et al. 3
  • 16
    • 0001064399 scopus 로고
    • Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547.
    • (1993) Angew. Chem. , vol.105 , pp. 576
    • Reiser, O.1
  • 17
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    • Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 547


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