Steric effects in the enantioselective transfer hydrogenation of 2- aroylacetates

Tetrahedron Asymmetry

Volumn 10, Issue 24, 1999, Pages 4663-4666

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

^a CNRS   (France)

^b PPG SIPSY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; ARYLACETIC ACID DERIVATIVE; BENZOYLACETIC ACID ESTER; EPHEDRINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ENANTIOMER; ESTERIFICATION; HYDROGENATION; PRIORITY JOURNAL; REACTION TIME; STEREOSPECIFICITY;

EID: 0033384475     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00540-6     Document Type: Article

References (11)

1. For a recent review, see: Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999,10, 2045-2061.
2. Everaere, K.; Carpentier, J.-F.; Mortreux, A.; Bulliard, M. Tetrahedron: Asymmetry 1998, 9, 2971-2974.
3. Schwink, L.; Ireland, T.; Püntener, K.; Knochel, P. Tetrahedron: Asymmetry 1998, 9, 1143-1163.
4. 2 precursor and N-substituted derivatives of (1S,2R)-norephedrine such as (1S,2R)-N-benzyl-norephedrine. Everaere, K.; Carpentier, J.-R; Mortreux, A.; Bulliard, M. Tetrahedron: Asymmetry 1999, 10, 4083-4086.
5. Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897-6898.
6. (a) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102.
7. (b) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
8. Kenny, J. A.; Palmer, M. J.; Smith, A. R. C.; Walsgrove, T.; Wills, M. Synlett 1999, 1615-1617.
9. Comble, L.; Jones, R.; Palmer, C. J. Chem. Soc., Perkin Trans. 1987, 317-332.
10. 1H} NMR, in agreement with literature data.
11. 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.