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Enantioselective hydrogenation of fluorinated unsaturated carboxylic acids over cinchona alkaloid modified palladium catalysts

Paper ID Volume ID Publish Year Pages File Format Full-Text
52071 46864 2008 4 PDF Available
Title
Enantioselective hydrogenation of fluorinated unsaturated carboxylic acids over cinchona alkaloid modified palladium catalysts
Abstract

The hydrogenation of trifluoromethyl substituted prochiral α,β-unsaturated carboxylic acids has been studied over cinchona alkaloid modified palladium heterogeneous catalysts. Low enantioselectivities were obtained in the hydrogenation of all three test compounds, 2-trifluoromethylacrylic acid, 4,4,4-trifluoro-3-methyl-2-butenoic acid and (E)-4,4,4-trifluoro-3-phenyl-2-butenoic acid, respectively. Significant increase in the enantioselectivity, up to 43%, was obtained in the hydrogenation of 4,4,4-trifluoro-3-methyl-2-butenoic acid by using benzylamine as additive. The presented results showed for the first time the possibility of enantioselective hydrogenation of α-unsubstituted β-disubstituted α,β-unsaturated carboxylic acids in the cinchonidine modified palladium catalytic system, that resulted in optically enriched saturated acids having the chiral center in β position.

Keywords
Carboxylic acids; Cinchonidine; Enantioselective; Fluorinated; Heterogeneous catalyst; Hydrogenation; Palladium
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Enantioselective hydrogenation of fluorinated unsaturated carboxylic acids over cinchona alkaloid modified palladium catalysts
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 9, Issue 3, 1 March 2008, Pages 421–424
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
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