Chiral Pyridinyloxazolidine Ligands for the Pd-Catalyzed Asymmetric Allylic Alkylation

Bulletin of the Korean Chemical Society

Volumn 24, Issue 9, 2003, Pages 1239-1240

  Yoon, Jin Koo ^a   Lee, Sang Joon ^a   Kim, Young Mok ^a   Jin, Myung Jong ^a  

^a Inha University   (South Korea)

Author keywords

Allylic alkylation; Asymmetric catalysis; Pd complex; Pyridinyloxazolidine

Indexed keywords

ALLYL COMPOUND; LIGAND; OXAZOLIDINE DERIVATIVE; PALLADIUM; PYRIDINYLOXAZOLIDINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; METAL BINDING; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0347595293     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2003.24.9.1239     Document Type: Article

References (19)

1. For recent reviews: (a) Togni, A.; Venanzi, L. M. Angew. Chem. Int. Ed. Engl. 1994, 33, 497.
2. (b) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395.
3. (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry, 1998, 9, 1.
4. (d) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336.
5. (a) von Matt, P.; Pfaltz, A.. Angew. Chem. Int. Ed. Engl. 1993, 32, 566.
6. (b) Sprinz, J.; Helmchen, G. Tetrahedron. Lett. 1993, 34, 1769.
7. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett 1993, 34, 3149.
8. (d) Steinhagen, H.; Reggelin, M.; Helmchen, G. Angew. Chem. Int. Ed. Engl. 1997, 36, 2108.
9. (e) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179.
10. (f) Pretot, R.; Pfaltz, A. Angew. Chem. Int. Ed. Engl. 1998, 37, 323.
11. (g) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227.
12. (h) Fukuta, T.; Takehara, A.; Iwao, M. Tetrahedron: Asymmetry 2001, 12, 2793.
13. (i) Ito, K.; Kashiwagi, R.; Hayashi, S.; Uchida, T.; Katsuki, T. Synlett 2001, 12, 284.
14. (j) Fukuda, T.; Takehara, A.; Iwao, M. Tetrahedron: Asymmetry 2001, 12, 2793.
15. Jin, M.-J.; Jung, J.-A.; Kim, S.-H. Tetrahedron Lett. 1999, 40, 5197.
16. 2O: C, 75.56; H, 7.13; N, 11.01. Found: C, 75.51; H, 7.18; N, 11.09.
17. The formation of cis-isomer of oxazolidine is favored under kinetic and thermodynamic conditions. (a) Beckett, A. H.; Jones, G. R. Tetrahedron 1977, 34, 3313.
18. (b) Mangeney, P.; Alexakis, A.; Normant, J. F. Tetrahedron 1984, 40, 1803.
19. (c) Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R. J. Org. Chem. 1988, 53, 1600.