Selective ruthenium-catalyzed epimerization of chiral sec-alcohols

Otto Långvik, Denys Mavrynsky, Reko Leino

Research output: Contribution to journalArticleScientificpeer-review

4 Citations (Scopus)

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).
Original languageUndefined/Unknown
Pages (from-to)255–259
Number of pages5
JournalCatalysis Today
Volume241
DOIs
Publication statusPublished - 2015
MoE publication typeA1 Journal article-refereed

Keywords

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

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