The role of acid in accelerating the asymmetric reduction of methyl acetoacetate with BINAP-chloro-(p-cymene)-Ru chloride complex

Journal of Molecular Catalysis A: Chemical

Volumn 217, Issue 1-2, 2004, Pages 21-26

  Wolfson, Adi ^a   Vankelecom, Ivo F J ^b   Geresh, Shimona ^c   Jacobs, Pierre A ^b  

^a NEGEV ACADEMIC COLLEGE OF ENGINEERING   (Israel)

^b UNIVERSITY OF LEUVEN   (Belgium)

^c BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

Author keywords

Asymmetric reduction; BINAP; Methyl acetoacetate

Indexed keywords

CATALYSIS; CHEMICAL BONDS; CHLORINE COMPOUNDS; HYDRIDES; HYDROGENATION;

CARBONYL BOND; HYDRID TRANSFER;

MOLECULAR STRUCTURE;

ACETOACETIC ACID; CHLORIDE; RUTHENIUM DERIVATIVE;

ACCELERATION; ACIDITY; ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; HYDROGENATION; IONIC STRENGTH; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 2542439654     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2004.03.014     Document Type: Article

References (26)

1. Klabunovskii E.I., Sheldon R.A. Cat. Tech. 1:1997;173
2. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
3. R. Noyori, M. Kitamura, N. Sayo, H. Kumobayashi, M. Giles, M. EP Patent No. 0 470 756 A2 (1991).
4. Akutagawa S. Appl. Catal. 128:1995;171
5. Ohta T., Takaya H., Noyori R. Tetrahedron Lett. 31:1990;7189
6. Ashby M.T., Halpern J. J. Am. Chem. Soc. 113:1991;589
7. Brown J.M., Rose M.R., Knight F.I., Wienand A. Rec. Trav. Chim. Pays-Bas. 114:1995;242
8. Noyori R., Ohkuma T., Kitamura M. J. Am. Chem. Soc. 109:1987;5856
9. Kitamura M., Ohkuma T., Inoue S., Sayo N., Kumobyashi H., Akutagawa S., Ohta T., Takaya H., Noyori R. J. Am. Chem. Soc. 110:1988;629
10. King S.A., Thompson A.S., King A.O., Verhoeven T.R. J. Org. Chem. 57:1992;6689
11. Hoke J.B., Hollis L.S., Stern E.W. J. Organomet. Chem. 455:1993;193
12. Gent J.P., Pinel C., Ratovelomana-Vidal V., Mallart S., Pfister X., Bischoff L., Cano De Andrate M.C., Darses S., Galopin C., Laffitte J.A. Tetrahedron Asymmetry. 5:1994;675
13. Mashima K., Kusano K., Sato N., Matsumura Y., Nozaki K., Kumobayashi H., Sayo N., Hori Y., Ishizaki T., Akutagawa S., Takaya H. J. Org. Chem. 59:1994;3064
14. Wolfson A., Vankelecom I.F.J., Jacobs P.A. J. Mol. Catal. A. 198:2002;39
15. Bayston D.J., Fraser J.L., Ashton M.R., Baxter A.D., Polywka M.E.C., Moses E.J. Org. Chem. 63:1998;3137
16. Guerreiro P., Ratovelomana-Vidal V., Genet J.P., Dellis P. Tetrahedron Lett. 42:2001;3423
17. Halle R.H., Colasson B., Schulz E., Spagnol M., Lemaire M. M. Tetrahedron Lett. 41:2000;643
18. Lamouille T., Saluzzo C., Halle R.T., Le Guyader F., Lemaire M. M. Tetrahedron Lett. 42:2001;663
19. Kockritz A., Bischoff S., Morawsky V., Pruße U., Vorlop K.D. J. Mol. Catal. A. 180:2002;231
20. D. Tas, C. Thoelen, I.F.J. Vankelecom, P.A. Jacobs, J. Chem. Soc., Chem. Commun. (1997) 2323.
21. Wolfson A., Vankelecom I.F.J., Jacobs P.A. Tetrahedron Lett. 44:2003;1195
22. King S.A., Thompson A.S., King A.O., Verhoeven T.R. J. Org. Chem. 57:1992;6689
23. J. March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, McGraw-Hill, 1992.
24. C. Girard, J.P. Genet, M. Bulliard, Eur. J. Org. Chem. (1999) 1937.
25. Moriasu M., Kato A., Hashimoto Y. J. Chem. Soc., Perkin Trans. 2:1984;905
26. W. Van Brussels, M. Renard, D. Tas. R. Parton, P.A. Jacobs, V.H. Rane, US Patent No. 5 997 840 (1999).