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Synthesis, Characterization and Catalytic Properties of Chiral BINOL Functionalized Mesoporous Silicas for Enantioselective Morita-Baylis-Hillman Reaction

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Abstract

Several Chiral BINOL functionalized mesoporous silicas were prepared by post grafting of organosilane derivatives of (S)-BINOL (1,1′-bi-2-naphthol) on SBA-15 and characterized by 13C CP/MAS NMR, FT-IR, UV–visible absorption spectra, elemental analysis, powder XRD, nitrogen adsorption–desorption isotherms and TEM techniques. Their catalytic properties were demonstrated in enantioselective Morita-Baylis-Hillman reaction of 3-phenylpropanal and cyclohexenone. Among them, 3BSBA-15 linked through the 3 position of BINOL exhibit higher enantioselectivity (26% e.e.) and yield (88%) which are similar to the homogeneous catalyst (S)-BINOL (27% e.e. and 92% yield) as Brønsted acids catalyst, while complex of 3BSBA-15 and calcium 3BSBA-15-Ca show lower enantioselectivity (21% e.e.) than its homogeneous complex (S)-BINOL-Ca (32% e.e.) as ligand catalyst. 3BSBA-15 and 3BSBA-15-Ca can be reused with no significant decrease in enantioselectivity and yield.

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Acknowledgment

We are grateful for the support for this study provided by the Distinguished Young Fund of Jilin Province, China (20050104).

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Authors and Affiliations

  1. State Key Laboratory of Polymer Physics and Chemistry, Chinese Academy of Sciences, Graduate School of the Chinese Academy of Sciences, 5625 Renmin Street, Changchun, 130022, People’s Republic of China

    Xiaomei Wang, Peng Han, Xiangling Ji & Lianxun Gao

  2. Laboratory of Polymer Engineering, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Graduate School of the Chinese Academy of Sciences, 5625 Renmin Street, Changchun, 130022, People’s Republic of China

    Xiaomei Wang, Peng Han, Xuepeng Qiu & Lianxun Gao

Authors
  1. Xiaomei Wang
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  2. Peng Han
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  3. Xuepeng Qiu
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  4. Xiangling Ji
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  5. Lianxun Gao
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Correspondence to Xiangling Ji or Lianxun Gao.

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Wang, X., Han, P., Qiu, X. et al. Synthesis, Characterization and Catalytic Properties of Chiral BINOL Functionalized Mesoporous Silicas for Enantioselective Morita-Baylis-Hillman Reaction. Catal Lett 124, 418–427 (2008). https://doi.org/10.1007/s10562-008-9495-4

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  • DOI: https://doi.org/10.1007/s10562-008-9495-4

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