Kinetic Resolution of Chiral Secondary Alcohols by Dehydrogenative Coupling with Recyclable Silicon-Stereogenic Silanes

Kinetic Resolution of Chiral Secondary Alcohols by Dehydrogenative Coupling with Recyclable Silicon-Stereogenic Silanes

Fishing for enantiomers: A novel kinetic resolution of racemic alcohols capable of two‐point binding makes use of silanes with silicon‐centered chirality. This strategy is based on a diastereoselective dehydrogenative silicon–oxygen coupling under copper catalysis (see scheme). The resolving silane...

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Veröffentlicht in:Angewandte Chemie International Edition 2005-11, Vol.44 (46), p.7620-7624
Hauptverfasser: Rendler, Sebastian, Auer, Gertrud, Oestreich, Martin
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemistry
asymmetric catalysis
Catalysis
copper
Copper - chemistry
dehydrogenation
Hydrogenation
kinetic resolution
Kinetics
Ligands
Molecular Conformation
Molecular Structure
Silanes - chemistry
silicon
Silicon - chemistry
Stereoisomerism
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Zusammenfassung:Fishing for enantiomers: A novel kinetic resolution of racemic alcohols capable of two‐point binding makes use of silanes with silicon‐centered chirality. This strategy is based on a diastereoselective dehydrogenative silicon–oxygen coupling under copper catalysis (see scheme). The resolving silane is completely recovered without erosion of stereochemical information at silicon.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200502631