Starting from commercially available ()- and ()-β-citronellol, two strategies were designed to synthesize all four stereoisomers of 2,6-dimethyloctane monoterpene chirons in four or five steps in 32-47% overall yield. The desired fragments were obtained by a key Ru-catalyzed asymmetric olefin hydrogenation step under moderate temperature (50 °C), pressure (4 bar), and low catalyst loadings (0.5 mol %) under optimized conditions. Screening of commercially available catalysts highlighted the key role of DM-SEGPHOS as an economically advantageous alternative to commonly used H8-BINAP for equal performances. These results open new possibilities for versatile and scalable syntheses of these useful building blocks.
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