Catalytic enantioselective ene reactions of imines: A simple approach for the formation of optically active α-amino acids

Chemical Communications

Volumn , Issue 22, 1998, Pages 2547-2548

  Yao, Sulan ^a   Fang, Xiangming ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALPHA AMINO ACID; IMINE; TOLUENESULFONIC ACID DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CATALYST; CHEMICAL REACTION; ENANTIOMER;

EID: 0032556461     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808019d     Document Type: Article

References (34)

1. Some recent books dealing with asymmetric catalysis: Advances in Catalytic Processes: Asymmetric Chemical. Transformations, ed. M. Doyle, JAI, Greenwich, CT, 1995, vol. 1;
2. Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, Weinheim, 1993;
3. M. Santelli and J.-M. Pons, Lewis Acids and Selectivity in Organic Synthesis, CRC Press, Boca Raton, 1995;
4. Asymmetric Catalysis in Organic Synthesis, ed. R. Noyori, Wiley Interscience, New York, 1993;
5. L. F. Tietze and G. Kettschau, Stereoselective Heterocyclic Synthesis I, ed. P. Metz, Springer Verlag, Berlin, 1997, vol. 189, pp. 1-120;
6. Transition Metals for Fine Chemicals and Organic Synthesis, ed. M. Beller and C. Bolm, Wiley Interscience, UK, 1998.
7. For a general review of eneantioselective ene reactions, see K. Mikami and M. Shimizu, Chem. Rev., 1992, 92, 1021.
8. See also e.g. K. Mikami, Pure Appl. Chem. 1996, 68, 639;
9. K. Mauruoka, Y. Hoshino, T. Shirasaka and H. Yamamoto, Tetrahedron Lett. 1988, 29, 3967;
10. D. A. Evans, C. S. Burgey, N. A. Paras and S. W. Tregay, J. Am. Chem. Soc., 1998, 120, 5824.
11. Examples of catalytic enantioselective hetero-Diels-Alder reactions of aldehydes and ketones see e.g. K. Maruoka, T. Otoh, T. Shirasaka and H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 310;
12. Q. Gao, K. Ishihara, M. Mouri and H. Yamamoto, Tetrahedron, 1994, 50, 979;
13. G. Keck, X.-Y. Li and D. Krishamurthy, J. Org. Chem., 1995, 60, 5998;
14. Q. Gai, T. Maruyama, M. Mouri and H. Yamamoto, J. Org. Chem., 1992, 57, 1951;
15. M. Bednarski and S. Danishefsky, J. Am. Chem. Soc., 1986, 108, 7060;
16. M. Johannsen and K. A. Jørgensen, J. Org. Chem., 1995, 60, 5757;
17. A. Graven, M. Johannsen and K. A. Jørgensen, Chem. Commun., 1996, 3272;
18. S. Yao, M. Johannsen, H. Audrian, R. G. Hazell and K. A. Jørgensen, J. Am. Chem. Soc., 1998, 120, 8599;
19. D. A. Evans and J. S. Johnson, J. Am. Chem. Soc., 1998, 120, 4895;
20. J. Thorhauge, M. Johannsen and K. A. Jørgensen, Angew. Chem., Int. Ed., 1998, 37, 2404
21. Examples of ene reactions of related imines with alkenes are: O. Achmatowicz and M. Pietraszkiewicz, J. Chem. Soc., Perkin Trans. 1, 1981, 2680;
22. D. M. Tschan and S. M. Weinreb, Tetrahedron Lett., 1982, 23, 3015;
23. K. Koch, J.-Y. Lin and F. W. Fowler, Tetrahedron Lett., 1983, 24, 1581;
24. D. M. Tschan, E. Turos and S. M. Weinreb, J. Org. Chem., 1984, 49, 5058;
25. S. Hannesian and R.-Y. Yang, Tetrahedron Lett., 1996, 30, 5273.
26. For catalytic enantioselective hetero-Diels-Alder reaction of imines: K. Ishihara, M. Miyata, H. Hattori and Y. Yamamoto, J. Am. Chem. Soc., 1994, 116, 10520;
27. S. Kobayashi, S. Komiyama and H. Ishitani, Angew. Chem., Int. Ed., 1998, 37, 797;
28. S. Yao, M. Johannsen, R. G. Hazell and K. A. Jørgensen, Angew. Chem., Int. Ed., 1998, in the press.
29. For catalytic enantioselective addition of enol silyl ethers to imines: E. Hagiwara, A. Fujii and M. Sodeeoka, J. Am. Chem. Soc., 1998, 120, 2474;
30. D. Ferraris, B. Young, T. Dudding and T. Lectka, J. Am. Chem. Soc., 1998, 120, 4548;
31. D. Ferraris, B. Young, C. Cox, W. J. Drury III, T. Dudding and T. Lectka, J. Org. Chem., 1998, 63, 6090.
32. For catalytic enantioselective alkylation of imines: H. Nakamura, K. Nakamura and Y. Yamamoto, J. Am. Chem. Soc., 1998, 120, 4242.
33. W. J. Drury III, D. Ferraris, C. Cox, B. Young and T. Lectka, J. Am. Chem. Soc., 1998, in the press.
34. 2 and stirred for 5 min; then the tosyl α-imino ester 2a (0.4 mmol) was added at room temp. The dark purple solution was cooled to the desired reaction temperature before the alkene (0.8 mmol) was added. Then the reaction was kept at that temperature until the dark purple colour had changed into a clear yellow solution (10-65 h). After evaporation of the solvent the crude product was purified by flash chromatography (20% EtOAc-pentane) to give the ene adduct.