Synthesis of chiral aminophosphines via nucleophilic aromatic substitution and their application to palladium-catalyzed enantioselective allylic substitution

Enantiomer

Volumn 2, Issue 3-4, 1997, Pages 203-213

  Hattori, Tetsutaro ^a   Komuro, Yasuko ^a   Hayashizaka, Noriyuki ^b   Takahashi, Hironori ^a   Miyano, Sotaro ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b Sumitomo Seika Chemicals Co Ltd   (Japan)

Author keywords

Allylic substitution; Dynamic NMR; EXSY Spectrum; Nucleophilic aromatic substitution; PM3 Calculation

Indexed keywords

PALLADIUM; PHOSPHINE DERIVATIVE;

CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; CONFERENCE PAPER; CONFORMATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

ALLYL COMPOUNDS; BENZENE DERIVATIVES; CATALYSIS; MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM; PHOSPHINES; STEREOISOMERISM;

EID: 0030794543     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Conference Paper

References (35)

1. Review: Hayashi, T. (1993). In Ojima, I. (editor), Catalytic Asymmetric Synthesis; VCH, New York, 325-365;
2. Reiser, O. (1993). Angew. Chem. Int. Ed. Engl., 32, 547;
3. Trost, B. M. and Van Vranken, D. L. (1996). Chem. Rev. 96, 395.
4. See also: Tokunoh, R., Sodeoka, M., Aoe, K. and Shibasaki, M. (1995). Tetrahedron Lett., 36, 8035.
5. von Matt, P. and Pfaltz, A. (1993). Angew. Chem. Int. Ed. Engl., 32, 566;
6. Sprinz, J. and Helmchen, G. (1993). Tetrahedron Lett., 34, 1769;
7. Dawson, G. J., Frost, C. G., Williams, J. M. J. and Coote, S. J. (1993). Tetrahedron Lett., 34, 3149.
8. Brown, J. M., Hulmes, D. I. and Guiry, P. J. (1994). Tetrahedron, 50, 4493.
9. Kubota, H. and Koga, K. (1994). Tetrahedron Lett., 35, 6689.
10. Brenchley, G., Merifield, E. and Wills, M. (1994). Tetrahedron Lett., 35, 2791;
11. Wimmer, P. and Widhalm, M. (1995). Tetrahedron: Asymmetry, 6, 657;
12. Minami, T., Okada, Y., Otaguro, T., Tawaraya, S., Furuichi, T. and Okauchi, T. (1995). Tetrahedron: Asymmetry, 6, 2469;
13. Knühl, G., Sennhenn, P. and Helmchen, G. (1995). J. Chem. Soc., Chem. Commun., 1845.
14. Reuman, M. and Meyers, A. I. (1985). Tetrahedron, 41, 837;
15. Gant, T. G. and Meyers, A. I. (1994). Tetrahedron, 50, 2297.
16. Hattori T., Hotta, H., Suzuki, T. and Miyano, S. (1993). Bull. Chem. Soc. Jpn., 66, 613;
17. Hattori, T., Koike, N., Okaishi, Y. and Miyano, S. (1996). Tetrahedron Lett., 37, 2057.
18. Hattori, T., Sakamoto, J., Hayashizaka, N. and Miyano, S. (1994). Synthesis, 199.
19. Cf.: Hattori, T., Suzuki, M., Komuro, Y. and Miyano, S. (1995). J. Chem. Soc., Perkin Trans. 1, 1473.
20. Casarini, D., Lunazzi, L., Alcaro, S., Gasparrini, F. and Villani, C. (1995). J. Org. Chem., 60, 5515.
21. Kessler, H. (1970). Angew. Chem. Int. Ed. Engl., 9, 219.
22. Trost, B. M. and Murphy, D. J. (1983). Organometallics, 4, 1143;
23. Leutenegger, U., Umbricht, G., Fahrni, C., von Matt, P. and Pfaltz, A. (1992). Tetrahedron, 48, 2143.
24. Trost, B. M. and Bunt, R. C. (1994). J. Am. Chem. Soc., 116, 4089.
25. Sprinz, J., Kiefer, M., Helmchen, G., Reggelin, M., Huttner, G., Walter, O. and Zsolnai, L. (1994). Tetrahedron Lett., 35, 1523.
26. Togni, A., Rihs, G., Pregosin, P. S. and Ammann, C. (1990). Helv. Chim. Acta, 73, 723.
27. Bandy, J. A., Green, M. L. H. and O'Hare, D. (1986). J. Chem. Soc., Dalton Trans., 2477.
28. Valk, J.-M., Claridge, T. D. W., Brown, J. M., Hibbs, D. and Hursthouse, M. B. (1995). Tetrahedron: Asymmetry, 6, 2597.
29. Short, R. P., Kennedy, R. M. and Masamune, S. (1989). J. Org. Chem., 54, 1755.
30. Berova, N. D. and Kurtev, B. J. (1969). Tetrahedron, 25, 2301;
31. Nakajima, M., Tomioka, K. and Koga, K. (1993). Tetrahedron, 49, 9735.
32. Kostyanovsky, R. G., Gella, I. M., Markov, V. I. and Samojlova, Z. E. (1974). Tetrahedron, 30, 39.
33. Sone, T., Hiroi, K. and Yamada, S. (1973). Chem. Pharm. Bull., 21, 2331.
34. Brunner, H. and Scheck, T. (1992). Chem. Ber., 125, 701.
35. Allen, J. V., Coote, S. J., Dawson, G. J., Frost, C. G., Martin, C. J. and Williams, J. M. J. (1994). J. Chem. Soc., Perkin Trans. 1, 2065.