Chiral pyridylmethyl- and quinolinyl-oxazolines as ligands for enantioselective palladium-catalyzed allylic alkylation

Tetrahedron Asymmetry

Volumn 10, Issue 7, 1999, Pages 1393-1400

  Chelucci, Giorgio ^a   Gladiali, Serafino ^a   Saba, Antonio ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

8 QUINOLINECARBOXYAMIDE; OXAZOLINE DERIVATIVE; OXAZOLINYLMETHYLPYRIDINE; OXAZOLINYLQUINOLINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033538141     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00114-7     Document Type: Article

References (20)

1. For reviews: Trost, M. B.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. For more recent references on palladium-catalyzed allylic alkylation reactions, see: Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 1604.
2. For reviews: Trost, M. B.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. For more recent references on palladium-catalyzed allylic alkylation reactions, see: Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 1604.
3. For reviews: Trost, M. B.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. For more recent references on palladium-catalyzed allylic alkylation reactions, see: Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 1604.
4. For reviews: Trost, M. B.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. For more recent references on palladium-catalyzed allylic alkylation reactions, see: Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 1604.
5. (a) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667.
6. (b) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183.
7. (c) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604.
8. (d) Nordström, K.; Macedo, E.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437.
9. Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1999, 10, 543. Chelucci, G.; Deriu, S.; Saba, A.; Valenti, R. Tetrahedron: Asymmetry 1999, 10, in press.
10. Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1999, 10, 543. Chelucci, G.; Deriu, S.; Saba, A.; Valenti, R. Tetrahedron: Asymmetry 1999, 10, in press.
11. Brunner, H. Angew. Chem., Int. Ed. Engl. 1993, 22, 897.
12. In the course of this work, synthesis of 2a and its use in asymmetric cyclopropanation was reported; the authors were unable to obtain 2b. Fryzuk, M. D.; Jafarpour, L.; Rettig, S. J. Tetrahedron: Asymmetry 1998, 9, 3191.
13. Blaser, H.-U. Chem. Rev. 1992, 92, 935.
14. When this manuscript was completed, a slightly different preparation of 3 appeared in print: Wu, X.-Y.; Li, X.-H.; Zhou, Q.-L. Tetrahedron: Asymmetry 1998, 9, 4143.
15. Bolm, C.; Veickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173.
16. Demmark, S. E.; Nakajiama, N.; Nicaise, O. J.-C.; Fauker, A. M.; Edwards, J. P. J. Org. Chem. 1995, 60, 4884 and references therein.
17. Högberg, T.; Ström, P.; Ebner, M.; Rämsby, S. J. Org. Chem. 1987, 52, 2033.
18. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143.
19. Blöchl, P. E.; Togni, A. Organometallics 1996, 15, 4125.
20. Elderfield, R. C.; Siegel, M. J. Am. Chem. Soc. 1951, 73, 5622.