Selective ruthenium-catalyzed epimerization of chiral sec-alcohols

• 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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