Interesting and effective P,N-chelation of tetrasubstituted ferrocene ligands for palladium-catalyzed asymmetric allylic substitution

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4545-4548

  Zhang, Wanbin ^a   Hirao, Toshikazu ^a   Ikeda, Isao ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; FERROCENE DERIVATIVE; LIGAND; PALLADIUM;

ARTICLE; CATALYSIS; CHELATION; DIASTEREOISOMER;

EID: 0030600179     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00899-4     Document Type: Article

References (28)

1. 1. a) Hayashi, T.; Yamamoto, A.; Hojo, M.; Ito, Y. J. Chem. Soc., Chem. Commun. 1989, 495-496.
2. b) Hayashi, T.; Yamamoto, A.; Hojo, M.; Kishi, K.; Ito, Y. J. Organomet. Chem. 1989, 370, 129-139.
3. 2. Zhang, W.; Adachi, Y.; Hirao, T. ; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451-460.
4. +.
5. 4 Park, J.; Lee, S.; Ahn, K. H.; Cho, C-H. Tetrahedron Lett. 1995, 36, 7263-7266.
6. 5 a) Nishibayashi, Y.; Uemura, S. Synlett. 1995, 79-81.
7. b) Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett. 1995, 74-76.
8. 2CH), 3.63 (1H, brs, FcH), 3.75 (1H, m, NCH), 3.91 (1H, dd, J 7.0, 8.2 Hz, OCH), 4.15 (5H, s, FcH), 4.18 (1H, dd, J 8.2, 9.4Hz, OCH), 4.42 (1H, brs, FcH), 4.88 (1H, brs, FcH), 7.13 (2H, m, PhH), 7.24 (3H, m, PhH), 7.40 (3H, m, PhH), 7.48 (2H, m, PhH).
9. 7. Reviews: a) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276.
10. b) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089-1122.
11. c) Hayashi, T. in 'Catalytic Asymmetric Synthesis', Ojima, I. Ed., VCH Publisher, New York, 1993, pp325-365,
12. d) Reiser, O. Angew. Chem. Int. Ed. Engl. 1993, 32, 547-549.
13. e) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
14. Selected papers: f) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138.
15. g) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796.
16. h) Brenchley, G.; Merifield, E.; Wills, M.; Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794.
17. i) Tanner, D.; Andersson, P. G.; Harden, A.; Somfai, P. Tetrahedron Lett. 1994, 35, 4631-4634.
18. j) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506.
19. k) Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066.
20. l) Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem. Int. Ed. Engl. 1995, 34, 2386-2388.
21. m) Seebach, D.; Devaquet, E.; Ernst, A.; Hayakawa, M.; Kuhnle, F. N. M.; Schweizer, W. B.; Weber, B. Helvetica Chimica Acta 1995, 78, 1636-1650.
22. n) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51-54.
23. o) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660.
24. p) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037.
25. 8. Selected papers: a) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772.
26. b) Matt, P-V.; Pfalts, A. Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568.
27. c) Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron: Asymmetry 1995, 6, 2535-2546.
28. 9 Hayashi, T.; Yamamoto, A.; Hagihara, T.; Ito, Y. Tetrahedron Lett. 1986, 27, 191-194.