Journal
TOPICS IN CATALYSIS
Volume 53, Issue 15-18, Pages 1002-1008Publisher
SPRINGER/PLENUM PUBLISHERS
DOI: 10.1007/s11244-010-9569-6
Keywords
Asymmetric transfer hydrogenation; Ruthenium; Iridium; Metallacycle; Dynamic kinetic resolution; Chlorohydrin; Epoxide; Haloalcohol dehalogenase
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Funding
- Netherlands Organisation for Scientific Research (NWO-CW/STW)
- Dutch Ministry of Economic Affairs, Royal DSM N.V
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Ruthenacycles, which are easily prepared in a single step by reaction between enantiopure aromatic amines and [Ru(arene)Cl-2](2) in the presence of NaOH and KPF6, are very good asymmetric transfer hydrogenation catalysts. A range of aromatic ketones were reduced using isopropanol in good yields with ee's up to 98%. Iridacycles, which are prepared in similar fashion from [IrCp*Cl-2](2) are excellent catalysts for the racemisation of secondary alcohols and chlorohydrins at room temperature. This allowed the development of a new dynamic kinetic resolution of chlorohydrins to the enantiopure epoxides in up to 90% yield and 98% enantiomeric excess (ee) using a mutant of the enzyme Haloalcohol dehalogenase C and an iridacycle as racemisation catalyst.
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