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Inversion of Enantioselectivity during the Platinum-Catalyzed Hydrogenation of an Activated Ketone

โœ Scribed by Matthias von Arx; Tamas Mallat; Alfons Baiker

Book ID
101366410
Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
89 KB
Volume
40
Category
Article
ISSN
0044-8249

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โœฆ Synopsis

Two competing reaction pathways, which lead to opposite enantiomers, occur in the hydrogenation of 1 over chirally modified platinum, as revealed by catalytic and NMR spectroscopic experiments: the fast reduction of the ketoform 1โ€‰a (minor species) and the slow hydrogenolysis of the hydrate 3 (major species).

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โœ Sheng-Mei Lu; Carsten Bolm ๐Ÿ“‚ Article ๐Ÿ“… 2008 ๐Ÿ› John Wiley and Sons ๐ŸŒ English โš– 294 KB ๐Ÿ‘ 2 views

We are grateful to the Fonds der Chemischen Industrie for financial support, and S.-M.L. thanks the Alexander von Humboldt Foundation for a postdoctoral fellowship. We also acknowledge Dr. C. Jaekel (BASF AG) for pointing out Refs. [5h] and [6].

Inversion of enantioselectivity in the h
Inversion of enantioselectivity in the hydrogenation of ketopantolactone on platinum modified by ether derivatives of cinchonidine
โœ Simon Diezi; Andras Szabo; Tamas Mallat; Alfons Baiker ๐Ÿ“‚ Article ๐Ÿ“… 2003 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 178 KB

Asymmetric hydrogenation of ketopantolactone was studied on a 5 wt% Pt/Al 2 O 3 catalyst in the presence of cinchonidine and its O-methyl, -ethyl, -phenyl and -trimethylsilyl derivatives. Inversion of enantioselectivity with the latter two bulky substituents proved that in the enantiodifferentiating