Improving conversion and enantioselectivity in hydrogenation by combining different monodentate phosphoramidites; a new combinatorial approach in asymmetric catalysis

Organic and Biomolecular Chemistry

Volumn 1, Issue 7, 2003, Pages 1087-1089

  Peña, Diego ^a   Minnaard, Adrian J ^a   Boogers, Jeroen A F ^b   De Vries, André H M ^b   De Vries, Johannes ^a,b   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b DSM RESEARCH   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CATALYST SELECTIVITY; COLUMN CHROMATOGRAPHY; HYDROGENATION; MIXING; MIXTURES; NITROGEN; RHODIUM; TRANSITION METALS;

ASYMMETRIC CATALYSIS; ENANTIOSELECTIVITY; MONODENTATE PHOSPHORAMIDITES;

ORGANIC COMPOUNDS;

EID: 0041495679     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b302097e     Document Type: Article

References (21)

1. (a) J. M. Brown, in Comprehensive Asymmetric Catalysis, eds. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer, Berlin, 1999, vol. 1, chapter 51
2. (b) P. A. Chaloner, M. A. Esteruelas, F. Joó and L. A. Oro, Homogeneous Hydrogenation, Kluwer, Dordrecht, 1994
3. (c) H. Brunner and W. Zettlmeier, Handbook of Enantioselective Catalysis, VCH, Weinheim, 1993.
4. (a) X. Zhang, Enantiomer, 1999, 4, 541
5. (b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley & Sons, New York, 1994, chapter 2.
6. I. V. Komarov and A. Börner, Angew. Chem., Int. Ed., 2001, 40, 1197.
7. (a) C. Claver, E. Fernandez, A. Gillon, K. Heslop, D. J. Hyett, A. Martorell, A. G. Orpen and P. G. Pringle, Chem. Commun., 2000, 961
8. (b) M. T. Reetz and G. Mehler, Angew. Chem., Int. Ed., 2000, 39, 3889
9. (c) M. van den Berg, A. J. Minnaard, E. P. Schudde, J. van Esch, A. H. M. de Vries, J. G. de Vries and B. L. Feringa, J. Am. Chem. Soc., 2000, 122, 11539.
10. (a) K. Mikami, S. Matsukawa, T. Volk and M. Terada, Angew. Chem., Int. Ed. Engl., 1997, 36, 2768
11. (b) H. Ishitani, S. Komiyama and S. Kobayashi, Angew. Chem., Int. Ed., 1998, 37, 3186
12. (c) R. Noyori, Angew. Chem., Int. Ed., 2002, 41, 2008
13. (d) For enantiomer-selective activation of racemic catalyst, see: K. Mikami and S. Matsukawa, Nature, 1997, 385, 613
14. (e) For a non metal-catalysed version, see: B. Kaptein, H. Elsenberg, A. J. Minnaard, Q. B. Broxterman, L. A. Hulshof, J. Koek and T. R. Vries, Tetrahedron: Asymmetry, 1999, 10, 1413
15. (f) For a related approach in ee determination, see: B. L. Feringa, A. A. Smaardijk and H. Wynberg, J. Am. Chem. Soc., 1985, 107, 4798.
16. M. T. Reetz, T. Sell, A. Meiswinkel and G. Mehler, Angew. Chem., Int. Ed., 2003, 42, 790.
17. D. Peña, A. J. Minnaard, J. G. de Vries and B. L. Feringa, J. Am. Chem. Soc., 2002, 124, 14552.
18. D. Peña, A. J. Minnaard, A. H. M. de Vries, J. G. de Vries and B. L. Feringa, Org. Lett., 2003, 5, 475.
19. M. van den Berg, A. J. Minnaard, R. M. Haak, M. Leeman, E. P. Schudde, A. Meetsma, B. L. Feringa, A. H. M. de Vries, C. E. P. Maliaars, C. E. Williams, D. Hyett, J. A. F. Boogers, H. J. W. Hendrickx and J. G. de Vries, Adv. Synth. Catal., 2003, 345, 308.
20. Reaction mixtures were prepared under argon in an automated way by a robot using stock solutions of precatalyst, ligands and substrates. See supplementary information † for experimental details and the whole set of results from a run.
21. This effect was not noticed when using a different solvent.