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Hydrogenation of β-isocinchonicine in mild conditions on Pt and Pd catalysts using HPLC-ESI-ion-trap MS: New results on the role of structure of cinchona alkaloids in the Orito reaction

Paper ID Volume ID Publish Year Pages File Format Full-Text
52816 46888 2006 5 PDF Available
Title
Hydrogenation of β-isocinchonicine in mild conditions on Pt and Pd catalysts using HPLC-ESI-ion-trap MS: New results on the role of structure of cinchona alkaloids in the Orito reaction
Abstract

The hydrogenation of β-isocinchonicine (β-ICNN) was studied on Pt- and Pd-alumina catalysts for the first time. Using mild experimental conditions (293 K, 1 bar hydrogen pressure) in toluene and in AcOH as solvents it was established that the enolo-ethereal CC double bond of β-ICNN is hydrogenated to the two DH-β-ICNN diastereomers. In toluene, hydrogenation proceeds at a significantly higher rate on Pd-alumina catalyst than on Pt-alumina. In AcOH, hydrogenation is fast on both catalysts. There was no significant difference between the selectivities of diastereomer formation on Pd and Pt catalysts. The presence of cinchonidine (CD) and cinchonine (CN) reduced the hydrogenation rate of β-ICNN and had no effect on the stereoselectivity of hydrogenation. Ethyl pyruvate (EtPy) hydrogenation on Pt-alumina catalyst modified with β-ICNN proceeded with low enantioselectivity, which is another piece of evidence for the essential role of the conformation of the chiral modifier in the Orito reaction.

Keywords
Hydrogenation; Enantioselective; β-Isocinchonicine; Pt- and Pd-catalysts; HPLC-ESI-ion-trap MS
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Hydrogenation of β-isocinchonicine in mild conditions on Pt and Pd catalysts using HPLC-ESI-ion-trap MS: New results on the role of structure of cinchona alkaloids in the Orito reaction
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 7, Issue 2, February 2006, Pages 104–108
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us