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Enantioselective hydrogenation of activated ketones in the presence of Pt–cinchona catalysts. Is the proton transfer concept valid?

Paper ID Volume ID Publish Year Pages File Format Full-Text
50173 46783 2014 4 PDF Available
Title
Enantioselective hydrogenation of activated ketones in the presence of Pt–cinchona catalysts. Is the proton transfer concept valid?
Abstract

•The Orito’s reaction was investigated in case of four different activated ketones.•The effect of achiral amines and nitrogen containing aromatics was studied.•According to proton transfer concept, the chiral and racem cycles would compete.•Achiral amine additives did not decrease the enantiomeric excess in either case.•Direct proton-transfer from Pt to the substrate via cinchonidine can be questioned.

Experimental evidences related to the proton transfer in the catalytic system Pt–cinchona alkaloids for enantioselective hydrogenation of activated ketones were collected and analyzed. Both new and earlier results indicate that in aprotic media direct transfer of proton from platinum to the substrate with the involvement of quinuclidine nitrogen as a general rule can be questioned.

Keywords
Proton transfer mechanism; Enantioselective hydrogenation; Activated ketones; Quinoline; Quinuclidine
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Enantioselective hydrogenation of activated ketones in the presence of Pt–cinchona catalysts. Is the proton transfer concept valid?
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 46, 10 February 2014, Pages 142–145
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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Price was $35.95
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