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Ruthenacycles and Iridacycles as Catalysts for Asymmetric Transfer Hydrogenation and Racemisation

By Nicolas Pannetier, Alexandre Holuigue, Vincent Ritleng, Arnaud J.A. Gayet, Florian Berthiol, Robert Haak, Thomas Jerphagnon, Gerard Verzijl, Laurent Lefort, Adeline Voelklin, Michel Pfeffer, Chiara Tarabiono, Dick B. Janssen, Adriaan J. Minnaard, Ben L. Feringa and Johannes G. de Vries

Abstract

Ruthenacycles, which are easily prepared in a single step by reaction between enantiopure aromatic amines and [Ru(arene)Cl2]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*Cl2]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.

Year: 2010
DOI identifier: 10.1007/s11244-010-9569-6
OAI identifier: oai:ub.rug.nl:dbi/4c6d21a517131

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Citations

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