Influence of a remote hydroxy group in the ligand on the reactivity of a chiral hydrogenation catalyst

Tetrahedron Asymmetry

Volumn 8, Issue 2, 1997, Pages 213-222

  Heller, Detlef ^a   Holz, Jens ^a   Borns, Susanne ^a   Spannenberg, Anke ^a   Kempe, Rhett ^a   Schmidt, Ute ^b   Börner, Armin ^a  

^a MAX PLANCK INSTITUTE FOR DEMOGRAPHIC RESEARCH   (Germany)

^b UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; HYDROXYL GROUP;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGEN BOND; HYDROGENATION; PRIORITY JOURNAL; REACTION ANALYSIS; X RAY ANALYSIS;

EID: 0031019330     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00522-8     Document Type: Article

References (45)

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6. Thus, simple change of the substrate may give rise to a decelerated catalysis (LDC): Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem. 1996, 108, 449; Angew. Chem. Int. Ed. Engl. 1996, 35, 451.
7. Thus, simple change of the substrate may give rise to a decelerated catalysis (LDC): Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem. 1996, 108, 449; Angew. Chem. Int. Ed. Engl. 1996, 35, 451.
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13. We have evidence that a properly situated hydroxy group in a conformationally flexible ligand coordinates on the rhodium: Heller, D.; Holz, J.; Borns, S.; Kempe, R.; Spannenberg, A.; Kless, A.; Baumann, W.; Börner, A. manuscript in preparation.
14. It is noteworthy, that with water as solvent remarkable effects concerning selectivity and activity have been described (e.g. Bakos, J.; Karaivanov, R.; Laghmari, M.; Sinou, D. Organometallics 1994. 13, 2951). It has to be verified, if any relations exist between these and our observations.
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20. 2 symmetry.
21. 2 (all data)=0.128, 837 parameters. Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at Cambridge Crystallographic Data Centre. Copies of the data can be obtained from: The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. (Telefax: Int. +44 1223/3 36 0 33; Email: teched@chemcrys.cam.ac.uk).
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33. The decelerating effect of the hydroxy group has been also qualitatively noted by other authors: a) Amma, J. P.; Stille, J. K. J. Org. Chem. 1982, 47, 468; Knowles, W. S.; Christopfel, W. C.; Koenig, K. E; Hobbs, C. F. 'Studies of Asymmetric Homogeneous Catalysts', in Catalytic Aspects of Metal Phosphane Complexes, Aleya, E. C.; Meek, D. W., Eds.; American Chemical Society, Washington, 1982, p. 325, 330.
34. The decelerating effect of the hydroxy group has been also qualitatively noted by other authors: a) Amma, J. P.; Stille, J. K. J. Org. Chem. 1982, 47, 468; Knowles, W. S.; Christopfel, W. C.; Koenig, K. E; Hobbs, C. F. 'Studies of Asymmetric Homogeneous Catalysts', in Catalytic Aspects of Metal Phosphane Complexes, Aleya, E. C.; Meek, D. W., Eds.; American Chemical Society, Washington, 1982, p. 325, 330.
35. In general, the HO-group bearing catalysts with the ligands 1a, 2a, 3a were superior in the hydrogenation of AMe compared to the parent catalysts, whereas in the case of AH the ee-differences were not significant (Ref. 10b).
36. obs. values cannot be traced back to changes of the absolute concentrations of catalyst - substrate complexes.
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39. Since trifunctional substrates have been hydrogenated, direct interactions with suitable situated functional groups of the substrate (e.g. carboxylic group) and the HO-group of the ligand cannot be excluded. Such interactions may occur by hydrogen bonds or other attractive interactions, respectively. However, due to the small differences in the catalytic performance of HO-catalyst and parent catalysts basic changes in the hydrogenation mechanism are unlikely (e.g. changed coordination mode of the substrate).
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42. Concerning the reaction order for hydrogen, see Ref. 17.
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