Ruthenium catalyzed asymmetric transfer hydrogenation of β-ketoesters

Tetrahedron Asymmetry

Volumn 9, Issue 17, 1998, Pages 2971-2974

  Everaere, Kathelyne ^a   Carpentier, Jean François ^a   Mortreux, André ^a   Bulliard, Michel ^b  

^a Ecole Nationale Superieure de Chimie de Lille   (France)

^b PPG SIPSY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; LIGAND BINDING; PRIORITY JOURNAL;

EID: 0032483323     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00325-5     Document Type: Article

References (12)

1. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102.
2. Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285-288.
3. Bernard, M.; Guiral, V.; Delbecq, F.; Fache, F.; Sautet, P.; Lemaire, M. J. Am. Chem. Soc. 1998, 120, 1441-1446 and references therein.
4. Jiang, Y.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1998, 120, 3817-3818.
5. Nishibayashi, Y.; Singh, J. D.; Arikawa, Y.; Uemura, S.; Hidai, M. J. Organomet. Chem. 1997, 531, 13-18.
6. Langer, T.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381-1384.
7. Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738-8739.
8. 2/TsDPEN affords 2d in 93% ee; see Ref. 1.
9. 2-diamine catalysts affords methyl mandelate in up to 99% ee; Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897-6898.
10. 50=turnover frequency expressed in mol of produced alcohol/mol of Ru.h and calculated at 50% conversion.
11. Schwink, L.; Ireland, T.; Püntener, K.; Knochel, P. Tetrahedron: Asymmetry 1998, 9, 1143-1163.
12. In every case, ee values were constant (±4%) throughout the whole reaction course, thus indicating that no significant racemization occurred with the present catalytic systems.