The detection of intermediates in the ruthenium(II) catalysed asymmetric hydrogenation of ketones using electrospray ionisation mass spectrometry

Chemical Communications

Volumn , Issue 1, 2000, Pages 99-100

  Kenny, Jennifer A ^a   Versluis, Kees ^b   Heck, Albert J R ^b   Walsgrove, Tim ^c   Wills, Martin ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b UTRECHT UNIVERSITY   (Netherlands)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; ENANTIOMER; HYDROGENATION; IONIZATION; MASS SPECTROMETRY; PROTON TRANSPORT;

EID: 0034614401     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908098h     Document Type: Article

References (15)

1. M. J. Palmer and M. Wills, Tetrahedron: Asymmetry, 1999, 10, 2045; R. Noyori and S. Hashiguchi, Acc. Chem. Res., 1997, 30, 97.
2. M. J. Palmer and M. Wills, Tetrahedron: Asymmetry, 1999, 10, 2045; R. Noyori and S. Hashiguchi, Acc. Chem. Res., 1997, 30, 97.
3. (a) J. Takehara, S. Hashiguchi, A. Fujii, S. Inoue, T. Ikariya and R. Noyori, Chem. Commun., 1996, 233;
4. (b) M. Palmer, T. Walsgrove and M. Wills, J. Org. Chem., 1997, 62, 5226;
5. (c) D. A. Alonso, D. Guijarro, P. Pinho, O. Temme and P. G. Andersson, J. Org. Chem., 1998, 63, 2749;
6. (d) J. A. Kenny, M. J. Palmer, A. R. C. Smith, T. Walsgrove and M. Wills, Synlett, 1999, 1615.
7. A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1996, 118, 2521; S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1995, 117, 7562; K. Matsumura, S. Hashiguchi, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1997, 119, 8738; K. Püntener, L. Schwink and P. Knochel, Tetrahedron Lett., 1996, 37, 8165.
8. A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1996, 118, 2521; S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1995, 117, 7562; K. Matsumura, S. Hashiguchi, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1997, 119, 8738; K. Püntener, L. Schwink and P. Knochel, Tetrahedron Lett., 1996, 37, 8165.
9. A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1996, 118, 2521; S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1995, 117, 7562; K. Matsumura, S. Hashiguchi, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1997, 119, 8738; K. Püntener, L. Schwink and P. Knochel, Tetrahedron Lett., 1996, 37, 8165.
10. A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1996, 118, 2521; S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1995, 117, 7562; K. Matsumura, S. Hashiguchi, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1997, 119, 8738; K. Püntener, L. Schwink and P. Knochel, Tetrahedron Lett., 1996, 37, 8165.
11. K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya and R. Noyori, Angew. Chem., Int. Ed. Engl., 1997, 36, 285.
12. M. A. Aramadia, F. Lafont, M. Morena-Manas, R. Pleixats and A. Roglans, J. Org. Chem., 1999, 64, 3592.
13. B. H. Lipshutz, J. Keith and D. J. Buzard, Organometallics, 1999, 18, 1571.
14. 2 solutions, were prepared in an analogous manner to those used in the transfer hydrogenation reactions described in ref. 2(b).
15. Mass spectra were acquired on a Micromass Platform single quadrupole instrument. Samples were introduced by loop injection at concentrations of 25 mM.