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Stereoselective hydrogenation of terpenes using platinum-based catalysts

“…The same tendency is followed as in the case of the hydrogenation of the double bond of a-pinene, but differences among the catalysts are not so marked. The verbenone behavior is analogous to the one observed in the case of pulegone hydrogenation with bi-and organobimetallic catalysts, and it is opposite to what occurs with a,b-unsaturated aldehydes [15,25]. Thus, in the case of verbenone, the C C bond is preferentially hydrogenated and the product of the selective hydrogenation of the C O bond, cis-verbenol, was not observed.…”

Synthesis of (−)‐menthol: Industrial synthesis routes and recent development

“…Vetere et al reported the hydrogenation of menthone (80% (−)-menthone, 20% (+)-isomenthone) over supported platinum catalysts. 147 Pt/SiO 2 showed a selectivity of 50% for (−)-menthol and 39% for (+)-neomenthol at 80% conversion. However, significant deactivation of the catalyst was observed.…”

A factorial design analysis of (+)-pulegone electrocatalytic hydrogenation

“…The reduction of natural terpenones in their respective alcohols is of great interest in food, pharmaceutical, chemical and cosmetic industries [39,40]. (+)-Pulegone belongs to the group of terpenones (flavours) that can be hydrogenated, generating (À)-menthone (1), (+)-isomenthone (2), (+)-neomenthol (3), (À)-menthol (4), (+)-neoisomenthol (5) and (À)-isomenthol (6).…”

“…In a second stage, 1 and 2 are slowly hydrogenated, generating four diastereoisomeric alcohols. Vetere et al [40] described the CH of (+)-pulegone as giving a mixture of all products: 1 (30%), 2 (28%), 3 (15%), 5 (16%), 4 (10%), 6 (1%).…”