On the role of planar chirality: A tunable enantioselectivity in palladium-catalyzed allylic alkylation with planar chiral 1,1'-P,N-ferrocene ligands

Chemical Communications

Volumn , Issue 4, 2000, Pages 285-286

  Deng, Wei Ping ^a   Hou, Xue Long ^a   Dai, Li Xin ^a   Yu, Yi Hua ^a   Xia, Wei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; FERROCENE DERIVATIVE; LIGAND; PALLADIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; ENANTIOMER; NONHUMAN; STEREOCHEMISTRY;

EID: 0034696215     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a909211k     Document Type: Article

References (29)

1. Reviews: I. Ojima, Catalytic Asymmetric Synthesis, VCH, New York, 1993; R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
2. Reviews: I. Ojima, Catalytic Asymmetric Synthesis, VCH, New York, 1993; R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
3. Review: H. Brunner and W. Zettimeier, Handbook of Enantioselective Catalysis with Transition Metal Compounds, VCH, Weinheim, 1993.
4. A. Togni, Angew. Chem., Int. Ed. Engl., 1996, 35, 1475; H.-U. Blaser and F. Spindler, Chimia, 1997, 51, 297; R. Imwinkelried, Chimia, 1997, 51, 300.
5. A. Togni, Angew. Chem., Int. Ed. Engl., 1996, 35, 1475; H.-U. Blaser and F. Spindler, Chimia, 1997, 51, 297; R. Imwinkelried, Chimia, 1997, 51, 300.
6. A. Togni, Angew. Chem., Int. Ed. Engl., 1996, 35, 1475; H.-U. Blaser and F. Spindler, Chimia, 1997, 51, 297; R. Imwinkelried, Chimia, 1997, 51, 300.
7. For reviews, see: (a) Ferrocenes, ed. A. Togni and T. Hayashi, VCH, Weinheim, 1995 and references therein;
8. (b) C. J. Richards and A. J. Locke, Tetrahedron: Asymmetry, 1998, 9, 2377.
9. (a) T. Hayashi, M. Konishi, M. Fukushima, T. Mise, M. Kagotani, M. Tajika and M. Kumada, J. Am. Chem. Soc., 1982, 104, 180;
10. (b) C. Bolm, K. M. Fernandez, A. Seger, G. Raabe and K. Gunther, J. Org. Chem., 1998, 63, 7860;
11. (c) X.-T. Zhou, Y.-R. Lin and L.-X. Dai, J. Org. Chem., 1999, 64, 1331.
12. (a) S.-L. You, Y.-G. Zhou, X.-L. Hou and L.-X. Dai, Chem. Commun., 1998, 2765;
13. (b) X. D. Du, L.-X. Dai, X.-L. Hou, L. J. Xia and M. H. Tang, Chin. J. Chem., 1998, 16, 90.
14. T. Sammakia and H. A. Latham, J. Org. Chem., 1995, 60, 6002; C. J. Richards, T. Damalidis, D. E. Hibbs and M. B. Hursthouse, Synlett, 1995, 74; Y. Nishibayashi and S. Uemura, Synlett, 1995, 79; J. Park, S. Lee, K. H. Ahn and C.-W. Cho, Tetrahedron Lett., 1995, 36, 7263.
15. T. Sammakia and H. A. Latham, J. Org. Chem., 1995, 60, 6002; C. J. Richards, T. Damalidis, D. E. Hibbs and M. B. Hursthouse, Synlett, 1995, 74; Y. Nishibayashi and S. Uemura, Synlett, 1995, 79; J. Park, S. Lee, K. H. Ahn and C.-W. Cho, Tetrahedron Lett., 1995, 36, 7263.
16. T. Sammakia and H. A. Latham, J. Org. Chem., 1995, 60, 6002; C. J. Richards, T. Damalidis, D. E. Hibbs and M. B. Hursthouse, Synlett, 1995, 74; Y. Nishibayashi and S. Uemura, Synlett, 1995, 79; J. Park, S. Lee, K. H. Ahn and C.-W. Cho, Tetrahedron Lett., 1995, 36, 7263.
17. T. Sammakia and H. A. Latham, J. Org. Chem., 1995, 60, 6002; C. J. Richards, T. Damalidis, D. E. Hibbs and M. B. Hursthouse, Synlett, 1995, 74; Y. Nishibayashi and S. Uemura, Synlett, 1995, 79; J. Park, S. Lee, K. H. Ahn and C.-W. Cho, Tetrahedron Lett., 1995, 36, 7263.
18. (a) W. Zhang, Y. Adachi, T. Hirao and I. Ikeda, Tetrahedron: Asymmetry, 1996, 7, 451;
19. (b) W. Zhang, Y. Yoneda, T. Kida, Y. Nakatsuji and I. Ikeda, Tetrahedron: Asymmetry, 1998, 9, 3371;
20. (c) J. Park, Z. Quan, S. Lee, K. H. Ahn and C.-W. Cho, J. Organomet. Chem., 1999, 584, 140;
21. (d) The 91% ee value of compound 22 using ligand 8 was obtained in our laboratory, which is consistent with Ikeda's result [ref. 8(b)]. However, Ahn et al. reported that 99% ee was obtained using the same ligand [ref. 8(c)];
22. (e) L. Schwink, T. Ireland, K. Puntener and P. Knochel, Tetrahedron: Asymmetry, 1998, 9, 1143.
23. A. Chesney, M. R. Bryce, R. W. J. Chubb, A. Batsanov and J. Howard, Synthesis, 1998, 413.
24. C. J. Richards and A. Mulvaney, Tetrahedron: Asymmetry, 1996, 7, 1419.
25. Selected papers for P,N-chelating ligands: (a) P.-V. Matt and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 1993, 32, 566;
26. (b) A. Togni, U. Burckhardt, V. Gramlich, P. S. Pregosin and R. Salzmann, J. Am. Chem. Soc., 1996, 118, 1031;
27. (c) I. Takei, Y. Nishibayashi, K. Segawa, Y. Arikawa, S. Uemura and M. Hidai, Organometallics, 1999, 18, 2271;
28. (d) O. Loiseleur, M. Hayashi, M. Keenan, N. Schmees and A. Pfaltz, J. Organomet. Chem., 1999, 576, 16.
29. B. M. Trost and D. Vranken, Chem. Rev., 1996, 96, 395.