A C2-symmetric nickel diamine complex as an asymmetric catalyst for enecarbamate additions to butane-2,3-dione

Organic and Biomolecular Chemistry

Volumn 3, Issue 16, 2005, Pages 2910-2913

  Fossey, John S ^a   Matsubara, Ryosuke ^a   Vital, Paulo ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATALYST ACTIVITY; COMPLEXATION; NICKEL COMPOUNDS; X RAY DIFFRACTION;

ALDOLS; SYMMETRIC COMPLEXES; SYMMETRIC DIAMINES; T-ALCOHOLS;

AMINES;

EID: 24144498694     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b505404d     Document Type: Article

References (22)

1. (a) R. Matsubara, P. Vital, Y. Nakamura, H. Kiyohara and S. Kobayashi, Tetrahedron, 2004, 60, 9769;
2. (b) R. Matsubara, Y. Nakamura and S. Kobayashi, Angew. Chem., Int. Ed., 2004, 43, 1679.
3. T. Arime, H. Takahashi, S. Kobayashi, S. Yamaguchi and N. Mori, Synth. Commun., 1995, 25, 389.
4. For structures of related nickel(II) complexes see: (a) L. Sacconi, I. Bertaini and F. Mani, Inorg. Chem., 1967, 6, 262;
5. (b) D. W. Evans, G. R. Newkome and F. R. Fronczek, Acta. Crystallogr., Sect. C, 1990, 46, 490;
6. (c) D. A. Handley, P. B. Hitchcock and G. J. Leigh, Inorg. Chim. Acta, 2001, 314, 1;
7. H. Ohtsu and K. Tanaka, Inorg. Chem., 2004, 43, 3024.
8. Overnight pre-mixing of ligand and metal triflate at rt was performed.
9. Conditions were selected based on previous work, see reference 1a.
10. 4 requires 340.1549).
11. For representative examples of nickel(II) complexes as chiral Lewisacids in catalysis see: (a) D. A. Evans, W. Downey and J. L. Hubbs, J. Am. Chem. Soc., 2003, 125, 8706;
12. (b) S. Kanemasa, Y. Oderaotoshi and E. Wada, J. Am. Chem. Soc., 1999, 121, 8675;
13. (c) S. Kanemasa, Y. Oderaotoshi, J. Tanaka and E. Wada, J. Am. Chem. Soc., 1998, 120, 12355;
14. (d) H. Suga, A. Kakehi and M. Mitsuda, Chem. Lett., 2002, 900;
15. (e) W. Zhuang, R. G. Hazell and K. A. Jørgensen, Chem. Commun., 2001, 1240;
16. (f) S. Iwasa, H. Maeda, K. Nishiyama, S. Tsushima, Y. Tsukamoto and H. Nishiyama, Tetrahedron, 2002, 58, 8281;
17. (g) H. Suga, T. Nakajima, K. Itoh and A. Kakehi, Org. Lett., 2005, 7, 1431.
18. See references 7b-c.
19. See reference 3c.
20. obsd × 3600).
21. 1H NMR spectroscopy only).
22. D. A. Evans, C. S. Burgey, M. C. Kowalski and S. W. Tregay, J. Am. Chem. Soc., 1999, 121, 686.