Asymmetric Hydrogenation of 3,4-Hexanedione over PtSn Catalysts

Abstract

In this work, some results of the liquid-phase racemic and enantioselective hydrogenation of 3,4-hexanedione are presented. The catalysts employed were platinum-based, supported on SiO 2 . Monometallic catalysts were modified with organotin precursors either chiral (hexa(-)-menthylditin, Men 3 Sn-SnMen 3 ) or achiral (tetrabutyltin, SnBu 4 ), and they were obtained via surface organometallic chemistry on metals techniques. Asymmetric system was selective to 4-hydroxyhexan-3-one, the enantiomeric excess achieved being 17%.

Novel access to epilupeol through chemoselective hydrogenation of lupenone using platinum-based organotin catalysts

“…In previous works, we studied the hydrogenation reactions of prochiral carbonyl compounds employing Pt catalysts modified with organotin precursors, either chiral or achiral, supported on silica. These systems were obtained using techniques derived from the Organometallic Surface Chemistry on Metals (SOMC/M), and proved to be active and selective in these hydrogenation reactions of interest in fine chemistry [12][13][14][15][16].…”

“…The procedures followed to prepare Pt and Pt-Sn catalysts have been previously published [14][15][16][17]. The monometallic catalyst was prepared by ionic exchange, using SiO 2 (Evonik, 180 m 2 /g) as support, which had been previously treated with an ammonia solution, under continuous stirring for 30 minutes at room temperature.…”