Nickel-catalyzed asymmetric multiple-component tandem coupling. Effects of simple monodentate oxazolines as chiral ligands

Journal of the American Chemical Society

Volumn 121, Issue 19, 1999, Pages 4712-4713

  Ikeda, Shin Ichi ^a   Ciu, Dong Mei ^a   Sato, Yoshiro ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; NICKEL; OXAZOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; OPTICAL ROTATION; REACTION ANALYSIS;

EID: 0344224279     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9844231     Document Type: Article

References (28)

1. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
2. (a) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
3. (b) Bunce, R. A. Tetrahedron 1995, 51, 13103.
4. Tietze, L. F. Chem. Rev. 1996, 96, 115.
5. (a) Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1994, 116, 5975.
6. (b) Ikeda, S.; Yamamoto, H.; Kondo, K.; Sato, Y. Organometallics 1995, 14, 5015.
7. (c) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248.
8. (d) Cui, D.-M.; Yamamoto, H.; Ikeda, S.; Hatano, K.; Sato, Y. J. Org. Chem. 1998, 63, 2782.
9. 3b For the nickel-catalyzed carbozincation of arylsubstituted internal alkynes, see: Stüdenmann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 93.
10. (a) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
11. (b) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887.
12. (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566.
13. (b) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769.
14. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. T. Tetrahedron Lett. 1993, 34, 3149.
15. Phaltz, A. Acc. Chem. Res. 1993, 26, 339.
16. (a) Brunner, H.; Obermann, U. Chem. Ber. 1989, 722, 499.
17. (b) Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173.
18. (a) Kurth, M. J.; Decker, O. H. W. J. Org. Chem. 1985, 50, 5789.
19. (b) Leonard, W. R.; Romine, J. L.; Meyers, A. I. J. Org. Chem. 1991, 56, 1961.
20. (c) Meyers, A. I.; Shipman, M. J. Org. Chem. 1991, 56, 7098.
21. (d) Kamata, K.; Agata, I.; Meyers, A. I. J. Org. Chem. 1998, 63, 3113.
22. 13C NMR spectra of diastereomeric ketal, which were obtained by the treatment of (+)-9c with (2R,3R)-2,3-butandiol; see: Lemière, G. L.; Dommisse, R. A.; Lepoivre, J. A.; Alderweireldt, F. C.; Hiemstra, H.; Wynberg, H.; Jones, J. B.; Toone, E. J. J. Am. Chem. Soc. 1987, 109, 1363.
23. 11d
24. (a) Racemate was already known, see: Wenkert, E.; Davis, L. L.; Mylari, B. L.; Solomon, M. F.; da Silva, R. R.; Shulman, S.; Warnet, R. J.; Ceccherelli, P.; Curini, M.; Pellicciari, R. J. Org. Chem. 1982, 47, 3242.
25. (b) Kokke, W. C. M. C.; Varkevisser, F. A. J. Org. Chem. 1974, 39, 1535.
26. (c) Posner, G. H.; Frye, L. L.; Hulce, M. Tetrahedron 1984, 40, 1401.
27. (d) Taura, Y.; Tanaka, M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1989, 30, 6349.
28. For the review including the examples of the enantioselective tandem reactions in the partially intermolecular and the fully intramolecular modes, see: Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371.