Selective ruthenium-catalyzed epimerization of chiral sec-alcohols

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Otto Långvik, Denys Mavrynsky, Reko Leino
Publisher: ELSEVIER SCIENCE BV
Publication year: 2015
Journal: Catalysis Today
Journal acronym: CATAL TODAY
Volume number: 241
Start page: 255
End page: 259
Number of pages: 5
ISSN: 0920-5861
eISSN: 1873-4308


Abstract

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).


Keywords

Epimerization, Homogeneous catalysis, Ruthenium, sec-Alcohol, Terpenoids

Last updated on 2019-08-12 at 04:04