Organogermanium compounds anchored on Pt/SiO2 as chiral catalysts for the enantioselective hydrogenation of 3,4-hexanedione

JULIO C. PODESTÁ; MARÍA BELÉN FARAONI; MARÍA BELÉN FARAONI; VIRGINIA VETERE; MÓNICA L. CASELLA; VIRGINIA VETERE; MÓNICA L. CASELLA; JULIO C. PODESTÁ

JOURNAL OF ORGANOMETALLIC CHEMISTRY

ELSEVIER SCIENCE SA

Lugar: Amsterdam; Año: 2018 vol. 863 p. 84 - 89

0022-328X

This work reports the synthesis of PtGe chiral catalysts using organogermanium compounds containing (-)-menthyl groups as substituents. Chiral inducers were carefully synthesized and characterized in order to obtain optically pure compounds.PtGe catalysts were prepared through a controlled surface reaction between the supported transition metal and the organometallic compound. This technique leads to reproducible and well defined phases. The catalysts were employed in the liquid phase enantioselective hydrogenation of 3,4-hexanedione.The systems obtained were active (95% conversion) and enantioselective (enantiomeric excess of 25% for 4-hydroxy-3-hexanone and 10% for 3,4-hexanediol). These results are very encouraging as they are comparable to those obtained previously by our group with similar PtSn catalysts and to those reported for classical Pt/cinchonidine systems.Organogermanium compounds presented here have advantages over their analogs tin, mainly due to their greater stability and non-toxicity.