Chiral oxazolinylpyridines as ligands for enantioselective palladium catalysed allylic substitution

Tetrahedron Asymmetry

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

  Chelucci, Giorgio ^a   Medici, Serenella ^a   Saba, Antonio ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

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

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

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

References (17)

1. Chelucci, G.; Berta, D.; Saba, A. Tetrahedron. 1997, 55, 3843 and references therein.
2. Chelucci, G. Tetrahedron: Asymmetry, 1997, in press.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 3).
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10. 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.
11. 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.
12. 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.
13. Trost, B. M.; Murphy, D. J. Organometallics, 1985, 4, 1143.
14. 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
15. Frost, C. G.; Williams, J. M. J. Tetrahedron Lett., 1993, 34, 2015.
16. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547.
17. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547.