Journal
JOURNAL OF MATERIALS CHEMISTRY
Volume 19, Issue 45, Pages 8580-8588Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b909002a
Keywords
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Funding
- National Natural Science Foundation of China [20621063, 20673113]
- National Basic Research Program of China [2009CB623503]
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The nanocomposites formed by SO3H-hollow-nanospheres and chiral amines are highly efficient catalysts for the direct asymmetric aldol reaction of cyclohexanone and 4-nitrobenzaldehyde. The catalyst showed 91% yield with 96% ee under optimized reaction conditions. SO3H-hollow-nanospheres were synthesized by oxidation of thiol-hollow-nanospheres, which were fabricated through a one-pot co-condensation of 1,2-bis(trimethoxysilyl) ethane and 3-mercaptopropyltrimethoxysilane around F127 micelles in the presence of NaOAc. Chiral amines could be combined with SO3H-hollow-nanospheres through facile electrostatic interactions. The obtained nanocomposites showed a much higher reaction rate than the catalyst formed from the combination of chiral amine and SO3H-mesoporous-organosilica (ribbon shaped particles with particle size of tens of micrometres) in the direct asymmetric aldol reaction. This is mainly attributed to the hollow spherical morphology and nano-scale particle size (16-20 nm) of the SO3H-hollow-nanospheres.
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