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Asymmetric Hydrogenation of Racemic 6‑Aryl 1,4-Dioxaspiro[4.5]decan-7-ones to Functionalized Chiral β‑Aryl Cyclohexanols via a Dynamic Kinetic Resolution

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journal contribution
posted on 11.02.2021, 20:47 by Dan Yang, Ai-Jiao Yang, Yong Chen, Jian-Hua Xie, Qi-Lin Zhou
A ruthenium-catalyzed asymmetric hydrogenation method for the synthesis of functionalized β-aryl cyclohexanols is described. With chiral spiro ruthenium catalyst (Ra,S,S)-5c, a series of racemic α-aryl cyclohexanones bearing a β-monoethylene ketal group were hydrogenated to the corresponding functionalized β-aryl cyclohexanols in high yields with enantioselectivity of up to 99% ee via a dynamic kinetic resolution. This protocol can be conducted on a decagram scale and provide potential approaches for the synthesis of optically active and densely functionalized aryl cyclohexanols.