Evaluation of Ligands for Ketone Reduction by Asymmetric Hydride Transfer in Water by Multi-Substrate Screening

• Published in: Advanced synthesis & catalysis Vol. 350; no. 1; pp. 197 - 204
• Main Authors: Zeror, Saoussen, Collin, Jacqueline, Fiaud, Jean-Claude, Zouioueche, Louisa Aribi
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 04.01.2008; WILEY‐VCH Verlag; Wiley
• Subjects: asymmetric catalysis; Chemistry; Chemistry, Applied; Chemistry, Organic; hydride transfer; multi-substrate screening; Physical Sciences; reduction; ruthenium; Science & Technology; SYSTEM; ORGANIC-SYNTHESIS; AROMATIC KETONES; hydride transfer; COMPLEXES; asymmetric catalysis; TRANSITION-METALS; ALCOHOLS; ruthenium; multi-substrate screening; CATALYZED ENANTIOSELECTIVE REDUCTION; reduction; TRANSFER-HYDROGENATION; CONJUGATE ADDITION
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.200700272

Various ligands for the ruthenium‐catalyzed enantioselective reduction of ketones in water have been investigated. Multi‐substrate reactions have been carried out for the comparison of various proline amides and aminoalcohol ligands. Two sets of six aromatic ketones have been selected in order to evaluate the enantiomeric excesses of all the resulting alcohols by a single chromatographic analysis. The proline amide derivative prepared from (1R,2S)‐cis‐aminoindanol revealed as the best ligand for most of the ketones used in the multi‐substrate reductions. This ligand has been employed for the enantioselective reduction of a variety of other aromatic ketones and in all cases the enantiomeric excesses were improved compared to those obtained with phenylprolineamide used in our previous work.