Palladium-catalyzed amination of allylic alcohols using anilines

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5000-5001

  Yang, Shyh Chyun ^a   Hung, Chung Wei ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; ANILINE DERIVATIVE; PALLADIUM;

AMINATION; ARTICLE; CATALYST; CHEMICAL BOND; ELECTRON; HEATING; ORGANIC CHEMISTRY; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0033039788     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990558t     Document Type: Article

References (28)

1. (a) Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Heidelberg, 1980.
2. (b) Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, p 799.
3. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985.
4. (d) Trost, B. M.; Fleming, I. In Comprehensive Organic Synthesis; Oppolzer, W., Ed.; Pergamon Press: New York, 1991; Vol. 5, p 315.
5. (e) Davis, J. A. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, p 291.
6. (f) Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 1995.
7. (a) Sakamoto, M.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1996, 69, 1065.
8. (b) Connell, R. D.; Rein, T.; Akermark, B.; Helquist, P. J. Org. Chem. 1988, 53, 3845.
9. (a) Trost, B. M. Tetrahedron 1977, 33, 371.
10. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385.
11. (c) Backvall, J. E. Acc. Chem. Res. 1983, 16, 335.
12. (d) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140.
13. (e) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173.
14. (f) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38.
15. (g) Tsuji, J. Synthesis 1990, 739.
16. (h) Trost, B. M. Pure Appl. Chem. 1992, 64, 315.
17. (i) Backvall, J. E. Pure Appl. Chem. 1992, 64, 429.
18. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
19. (a) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y. Tetrahedron Lett. 1982, 23, 4809.
20. (b) Trost, B. M.; Hung, M. H. J. Am. Chem. Soc. 1983, 105, 7757.
21. (c) Takahashi, T.; Jinbo, Y.; Kitamura, K.; Tsuji, J. Tetrahedron Lett. 1984, 25, 5921.
22. (d) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y.; Sugihara, T.; Takahashi, K. J. Org. Chem. 1985, 50, 1523.
23. (a) Lumin, S.; Falck, J. R.; Capdevila, J.; Karara, A. Tetrahedron Lett. 1992, 33, 2091.
24. (b) Tsay, S.; Lin, L. C.; Furth, P. A.; Shum, C. C.; King, D. B.; Yu, S. F.; Chen, B.; Hwu, J. R. Synthesis 1993, 329.
25. (c) Masuyama, Y.; Kagawa, M.; Kurusu, Y. Chem. Lett. 1995, 1121.
26. Stary, I.; Stara, I. G.; Kocovsky, P. Tetrahedron Lett. 1993, 34, 179.
27. Itoh, K.; Hamaguchi, N.; Miura, M.; Nomura,M. J. Chem. Soc., Perkin Trans. 1 1992, 2833.
28. 2 to Pd(O) species: Satoh, T.; Itoh, K.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1993, 66, 2121.