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Selective ruthenium-catalyzed epimerization of chiral sec-alcohols

Paper ID Volume ID Publish Year Pages File Format Full-Text
54343 47006 2015 5 PDF Available
Title
Selective ruthenium-catalyzed epimerization of chiral sec-alcohols
Abstract

•Selective catalytic epimerization of readily available chiral secondary alcohols is demonstrated.•Rapid and inexpensive formation of the less abundant diastereomers is achieved under mild conditions.•Epicholesterol is produced by epimerization of cholesterol.

Extension of secondary alcohol racemization catalyzed by homogeneous half-sandwich ruthenium complexes to the epimerization of natural products containing additional non-functionalized stereo-centers has been investigated. Ruthenium-catalysed epimerization of the sec-alcohols (−)-menthol, (−)-isopulegol, (+)-borneol, (+)-fenchol and cholesterol under mild reaction conditions and low catalyst loadings (2 mol%) provides rapid access to their less abundant diastereoisomers (+)-neomenthol, (+)-neoisopulegol, isoborneol, beta-fenchol and epicholesterol in admixture with the parent diastereomers in ratios ranging from 1:4.9 to 1:2.4 (epimer:parent).

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Keywords
Epimerization; Terpenoids; sec-Alcohol; Homogeneous catalysis; Ruthenium
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Selective ruthenium-catalyzed epimerization of chiral sec-alcohols
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Today - Volume 241, Part B, 1 March 2015, Pages 255–259
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
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Price was $35.95
You save - $31
Price after discount Only $4.95
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Full-text PDF Download
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