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Enantioselective hydrogenation of exocyclic α,β-unsaturated ketones: Part II. Hydrogenation in the presence of (S)-proline

✍ Scribed by Gabriella Fogassy; Antal Tungler; Albert Lévai; Gábor Tóth

Publisher
Elsevier Science
Year
2002
Tongue
English
Weight
74 KB
Volume
179
Category
Article
ISSN
1381-1169

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✦ Synopsis

In the asymmetric synthesis of chiral compounds, the reduction of prochiral unsaturated reactants has a great importance.

(S)-proline as a chiral auxiliary is used in the hydrogenations of exocyclic ␣,␤-unsaturated ketones with palladium on carbon catalysts, producing the corresponding saturated ketones with an optical purity up to 20%. The influence of the parameters (solvents, additives) on the optical yield is also investigated. The highest enantioselectivity was obtained in ethyl acetate and acetonitrile (ee 20%), at atmospheric pressure and room temperature.

📜 SIMILAR VOLUMES

Selective hydrogenation of exocyclic α,β
Selective hydrogenation of exocyclic α,β-unsaturated ketones:: Part I. Hydrogenations over palladium
✍ Gabriella Fogassy; László Hegedűs; Antal Tungler; Albert Lévai; Tibor Máthé 📂 Article 📅 2000 🏛 Elsevier Science 🌐 English ⚖ 261 KB

Exocyclic a ,b-unsaturated ketones were hydrogenated to the corresponding saturated ketones with Pd catalysts. The effect of solvents, basic and poisoning additives and various supports on conversion and selectivity was investigated. The conditions, under which the reaction afforded the saturated ke