Ferrocenyl ligands with two phosphanyl substituents in the α,ε positions for the transition metal catalyzed asymmetric hydrogenation of functionalized double bonds

Angewandte Chemie - International Edition

Volumn 38, Issue 21, 1999, Pages 3212-3215

  Ireland, Tania ^a   Grossheimann, Gabriele ^a   Wieser Jeunesse, Catherine ^a   Knochel, Paul ^a  

^a NONE

Author keywords

Asymmetric catalysis; Homogeneous catalysis; Hydrogenations; Metallocenes; Phosphanes

Indexed keywords

FERROCENE DERIVATIVE; LIGAND; PHOSPHANILIC ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; HYDROGENATION;

EID: 0033517686     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991102)38:21<3212::AID-ANIE3212>3.0.CO;2-9     Document Type: Article

References (22)

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19. However, preliminary experiments show that 2-substituted β-dicarbonyl compounds give moderate diastereoselectivities but also excellent enantioselectivities under our conditions. Hydrogenation of ethyl 2-methyl-3-oxo-butyrate with ligand 2a affords ethyl 3-hydroxy-2-methyl-butyrate with 40% de, 91.4% ee (2R,3S), and 86.0% ee (2S,3S).
20. Enantiomeric excesses were determined by GC or HPLC on a chiral phase (Chirasil-L-Val, and Diacel Chiralcel columns OD, OJ, AD).
21. 2 by full-matrix least-squares methods (SHELXS-97, SHELXL-97, SHELDRICK, 1997). All non-hydrogen atoms were refined anisotropically. ωR2 = 0.0893 (all unique data), R1 = 0.0367 for data with I>2σ(I). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-134965. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CD21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam. ac.uk).
22. P,Rh = 155.1 Hz).