Homogeneous silicone modified primary amine-Brønsted acid salt catalyzed aldol reaction: unexpected synergistic effect of polysiloxane with remarkable improvement of efficiency and stereoselectivity |
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| Authors: | Li-Wen Xu Ya-Dong Ju Hua-Yu Qiu Guo-Qiao Lai |
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| Institution: | a Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012, PR China
b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China |
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| Abstract: | We have developed a new strategy to improve the stereoselectivity in enamine catalysis by the introduction of super-hydrophobic long-chain silicone/polysiloxane as support/functional group for a model aldol reaction. The homogeneous direct aldol reaction of cyclic ketones with different aromatic aldehydes catalyzed by polysiloxane-derived primary amines has been reported with high yields, good diastereoselectivity, and up to 99% ee. |
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| Keywords: | Enamine catalysis Primary amine Aldol reaction Polysiloxane Organocatalysis |
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