RuCl3/PPh3: an efficient combination for the preparation of chiral 1,3-anti-diols through catalytic hydrogenation.
[reaction: see text] An efficient economical alternative to the commonly used Evans' reagent for the diastereoselective reduction of beta-hydroxy ketones is reported. Thus, ruthenium-mediated hydrogenation of enantioenriched beta-hydroxy ketones using RuCl3 associated to achiral monophosphines allowed the preparation of a series of 1,3-anti-diols in good yields and with a high level of diastereoselectivity. A short screening of ligands pointed out PPh3 as the most effective phosphine, and PCy3 afforded the 1,3-diols with an unexpected moderate syn selectivity.
Labeeuw
Olivier
O
Laboratoire de Synthèse Sélective Organique et Produits Naturels UMR 7573 CNRS, ENSCP, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France.
Roche
Christophe
C
Phansavath
Phannarath
P
Genêt
Jean-Pierre
JP
D002384:Catalysis; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D017975:Ruthenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
D009943:Organophosphorus Compounds; D017975:Ruthenium Compounds; D014867:Water; C061896:triphenylphosphine; C038365:ruthenium chloride