Chiral phosphinooxazolidine ligand derived from prolinol: Application to the Pd-catalyzed asymmetric allylic alkylation

Bulletin of the Korean Chemical Society

Volumn 23, Issue 10, 2002, Pages 1487-1489

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

^a Inha University   (South Korea)

Author keywords

Allylic alkylation; Asymmetric catalysis; Pd complex; Phosphinooxazolidine

Indexed keywords

ALLYL COMPOUND; OXAZOLIDINE DERIVATIVE; PALLADIUM COMPLEX; PHOSPHINOOXAZOLIDINE; PROLINOL; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHIRALITY; CONFORMATION; DIASTEREOISOMER; MOLECULAR RECOGNITION; OPTICAL ROTATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 0037145550     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2002.23.10.1487     Document Type: Article

References (21)

1. (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. Pfaltz, A.; Lautens, M. Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Yamamoto, H., Eds.; Springer: Heidelberg, 1999.
6. (a) von Matt, P; Pfaltz, A. Angew. Chem. Int. Ed. Engl. 1993, 32, 566.
7. (b) Sprinz, J.; Helmchen, G.; Tetrahedron Lett. 1993, 34, 1769.
8. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149.
9. (d) Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron: Asymmetry 1995, 6, 2535.
10. (e) Newmann, L. M.; Williams, J. M. J. Tetrahedron: Asymmetry 1996, 7, 1597.
11. (f) teinhagen, H.; Reggelin, M.; Helmchen, G. Angew. Chem. Int. Ed. Engl. 1997, 36, 2108.
12. (g) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179.
13. (h) Pretot, R.; Pfaltz, A. Angew. Chem. Int. Ed. Engl. 1998, 37, 323.
14. (i) Kudis, S.; Helmchen, G. Angew. Chem. Int. Ed. Engl. 1998, 37, 3047.
15. (j) Imai, Y.; Zhang, W.; Kida, T; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343.
16. (k) Fukuda, T; Takehara, A.; Iwao, M. Tetrahedron: Asymmetry 2001, 12, 2793.
17. Jin, M.-J.; Jung, J.-A.; Kim, S.-H. Tetrahedron Lett. 1999, 40, 5197.
18. 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.
19. (b) Mangeney, P.; Alexakis, A.; Normant, J. F. Tetrahedron 1984, 40, 1803.
20. (c) Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R. J. Org. Chem 1988, 53, 1600.
21. Dierkes, P.; Ramdeehul, S.; Barloy, L.; Cian, A. D.; Fischer, J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Osborn, J. A. Angew. Chem. Int. Ed. Engl. 1998, 37, 3116.