Thermomorphic system with non-fluorous phase-tagged Ru(BINAP) catalyst: facile liquid/solid catalyst separation and application in asymmetric hydrogenation.

Yi-Yong Huang; Yan-Mei He; Hai-Feng Zhou; Lei Wu; Bao-Lin Li; Qing-Hua Fan

doi:10.1021/jo052092m

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Thermomorphic system with non-fluorous phase-tagged Ru(BINAP) catalyst: facile liquid/solid catalyst separation and application in asymmetric hydrogenation.

Yi-Yong Huang·Yan-Mei He·Hai-Feng Zhou·Lei Wu·Bao-Lin Li·Qing-Hua Fan

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Abstract

The thermomorphic BINAP derivative 1 tagged with long alkyl chains was prepared from (S)-5,5'-diamino BINAP and applied to Ru-catalyzed asymmetric hydrogenation of beta-ketoesters under homogeneous conditions in 3:1 (v/v) ethanol/1,4-dioxane at 60 degrees C with high enantioselectivity (up to 98% ee). Results indicated that the Ru(1) catalyst was easily recovered by simple cooling and precipitation and could be used for at least four cycles without any loss of enantioselectivity.

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Alcohols Catalysis Esters Hydrogenation Ketones Ligands Molecular Structure Organometallic Compounds Ruthenium Stereoisomerism Temperature Journal Article Research Support, Non-U.S. Gov't

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Yi-Yong Huang, Yan-Mei He, Hai-Feng Zhou, Lei Wu, Bao-Lin Li, Qing-Hua Fan. 2006-03-31. Thermomorphic system with non-fluorous phase-tagged Ru(BINAP) catalyst: facile liquid/solid catalyst separation and application in asymmetric hydrogenation.. https://doi.org/10.1021/jo052092m

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