Selective ruthenium-catalyzed epimerization of chiral sec-alcohols

A1 Originalartikel i en vetenskaplig tidskrift (referentgranskad)


Interna författare/redaktörer


Publikationens författare: Otto Långvik, Denys Mavrynsky, Reko Leino
Förläggare: ELSEVIER SCIENCE BV
Publiceringsår: 2015
Tidskrift: Catalysis Today
Tidskriftsakronym: CATAL TODAY
Volym: 241
Artikelns första sida, sidnummer: 255
Artikelns sista sida, sidnummer: 259
Antal sidor: 5
ISSN: 0920-5861
eISSN: 1873-4308


Abstrakt

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).


Nyckelord

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

Senast uppdaterad 2020-29-01 vid 07:36