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

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

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

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Veröffentlicht in:Angewandte Chemie International Edition 2001-06, Vol.40 (12), p.2302-2305
Hauptverfasser: von Arx, Matthias, Mallat, Tamas, Baiker, Alfons
Format: Artikel
Sprache:eng
Schlagworte:
asymmetric hydrogenation
chiral auxiliaries
heterogeneous catalysis
hydrates
platinum
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Beschreibung
Zusammenfassung:Two competing reaction pathways, which lead to opposite enantiomers (see scheme), occur in the hydrogenation of 1 over chirally modified platinum, as revealed by catalytic and NMR spectroscopic experiments: the fast reduction of the ketoform 1 a (minor species) and the slow hydrogenolysis of the hydrate 3 (major species).
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20010618)40:12<2302::AID-ANIE2302>3.0.CO;2-P