Novel silica-based hybrid materials incorporating binaphthyl units: a chiral matrix effect in heterogeneous asymmetric catalysis |
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| Institution: | 1. State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029, China;2. Beijing Key Laboratory of Energy Environmental Catalysis, Beijing University of Chemical Technology, Beijing 100029, China;3. China Tianchen Engineering Corporation (Beijing Branch), Beijing 100029, China;1. Department of Chemistry, The University of Burdwan, Golapbag, Burdwan 713 104, India;2. Bio-Organic Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400 085, India |
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| Abstract: | Polysilsesquioxane hybrid materials containing chiral binaphthyl moieties are readily available by coupling (R)- or (S)-2,2′-dihydroxy-1,1′-binaphthyl (BINOL) with 3-(triethoxysilyl)propyl isocyanate and subsequent hydrolysis polycondensation of the resulting bis-trialkoxysilylated carbamate precursor. Rhodium species were embedded in the chiral hybrid matrix. The catalytic properties of the solids were evaluated in hydride-transfer reduction to prochiral ketones. When the catalytic species were embedded in an entirely chiral network, enantiomeric excesses up to 45% were observed. |
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