Synthesis of a new water-soluble C2-symmetric chiral diamine: Preliminary investigation of its catalytic properties for asymmetric hydrogenation under biphasic conditions

Journal of Organic Chemistry

Volumn 67, Issue 23, 2002, Pages 8191-8196

  Maillet, Céline ^a   Praveen, Thoniyot ^a   Janvier, Pascal ^a   Minguet, Sébastien ^b   Evain, Michel ^c   Saluzzo, Christine ^d   Tommasino, M Lorraine ^d   Bujoli, Bruno ^a  

^a Centre National de la Recherche Scientifique   (France)

^b UFR SCIENCES ET TECHNIQUES   (France)

^c INSTITUT DES MATÉRIAUX JEAN ROUXEL   (France)

^d CPE LYON   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; HYDROGENATION; IRIDIUM COMPOUNDS; KETONES; SYNTHESIS (CHEMICAL);

AROMATIC RINGS;

AMINES;

ACETOPHENONE; DIAMINE; IRIDIUM COMPLEX; KETONE; LIGAND; METHANOL; N,N' DIMETHYL 1,2 DIPHENYLETHANE 1,2 DIAMINE; ORGANOMETALLIC COMPOUND; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHIRALITY; HYDROGENATION; REACTION ANALYSIS; SOLUBILITY; SYNTHESIS;

EID: 0037111705     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020506v     Document Type: Article

References (29)

1. For a detailed review, see: (a) Aqueous Phase Organometallic Catalysis: Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
2. (b) Cornils, B.; Herrmann, W. A.; Eckl, R. W. J. Mol. Catal. A: Chem. 1997, 116, 27-33.
3. (a) Rhône-Poulenc Recherche (Kuntz, E.). FR Patent 2.314.910, 1975. Kuntz, E. G. Chem. Technol. 1987, 570-575.
4. (a) Rhône-Poulenc Recherche (Kuntz, E.). FR Patent 2.314.910, 1975. Kuntz, E. G. Chem. Technol. 1987, 570-575.
5. (b) Sheldon, R. A. C. R. Acad. Sci. Paris, Série IIc, Chem. 2000, 3, 541-551.
6. (c) Grosselin, J. M.; Mercier, C.; Grass, F. Organometallics 1991, 10, 2126-2133.
7. (a) Schull, T. L.; Fettinger, J. C.; Knight, D. A. J. Chem. Soc., Chem. Commun. 1995, 1487-1488.
8. (b) Schull, T. L.; Fettinger, J. C.; Knight, D. A. Inorg. Chem. 1996, 35, 6717-6723.
9. (c) Lelièvre, S.; Mercier, F.; Mathey, F. J. Org. Chem. 1996, 61, 3531-3533.
10. (d) Penicaud, V.; Maillet, C.; Janvier, P.; Pipelier, M.; Bujoli, B. Eur. J. Org. Chem. 1999, 1745-1748.
11. (e) Dressick, W. J.; George, C.; Brandow, S. L.; Schull, T. L.; Knight, A. J. Org. Chem. 2000, 65, 5059-5062.
12. (f) Kant, M.; Bischoff, S.; Siefken, R.; Gründemann, E.; Köckritz, A. Eur. J. Org. Chem. 2001, 477-481.
13. (g) Bischoff, S.; Kant, M. Catal. Today 2001, 66, 183-189.
14. (h) Köckritz, A.; Bischoff, S.; Kant, M.; Siefken, R. J. Mol. Catal. A: Chem. 2001, 174, 119-126.
15. Clearfield, A. In Progress in Inorganic Chemistry Karlin, K. D., Ed.; Wiley & Sons: New York, 1998; pp 371-510.
16. Alexakis, A.; Aujard, I.; Kanger, T.; Mangeney, P. Org. Synth. 1999, 76, 23-36.
17. (a) Noyori, R. In Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
18. (b) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40-73.
19. (c) Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159-2231.
20. (a) Tommasino, M. L.; Thomazeau, C.; Touchard, F.; Lemaire, M. Tetrahedron: Asymmetry 1999, 10, 1813-1819.
21. (b) Bernard, M.; Guiral, V.; Delbecq, F.; Fache, F.; Sautet, P.; Lemaire, M. J. Am. Chem. Soc. 1998, 120, 1441-1446.
22. For very large-scale preparations, a limiting step is the separation of meso-2b and d,l-2b by column chromatography. To overcome this problem, this mixture can be treated by acetaldehyde to form meso-3 and d,l-3. The aminal d,l-3 was selectively crystallized out of acetonitrile, and after hydrolysis under acidic conditions, d,l-2b was recovered and used for the separation of the d and l isomers (yield of d,l-2b isolated from a meso-2b and d,l-2b mixture on a 30 g scale: 79%). See Supporting Information.
23. Hirao, T.; Masunage, T.; Yoshiro, O.; Agawa, T. Synthesis 1981, 56-57.
24. Penicaud, V.; Odobel, F.; Bujoli, B. Tetrahedron Lett. 1998, 39, 3689-3692.
25. McKenna, C. E.; Higa, M. T.; Cheung, N. H., McKenna, M. C. Tetrahedron Lett. 1977, 155-158.
26. Thorpe, T.; Blacker, J.; Brown, S. M.; Bubert, C.; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Williams, J. M. J. Tetrahedron Lett. 2001, 42, 4041-4043.
27. Touchard, F.; Bernard, M.; Fache, F.; Lemaire, M. J. Mol. Catal. A: Chem. 1999, 140, 1-11.
28. (a) Maillet, C.; Janvier, P.; Pipelier, M.; Praveen, T.; Andres, Y.; Bujoli, B. Chem. Mater. 2001, 13, 2879-2884.
29. (b) Maillet, C.; Janvier, P.; Bertrand, M.; Praveen, T.; Bujoli, B. Eur. J. Org. Chem. 2002, 1685-1689.