Chinese Journal of Catalysis ›› 2015, Vol. 36 ›› Issue (3): 367-371.DOI: 10.1016/S1872-2067(14)60248-5

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Chitosan- supported cinchonine as an efficient organocatalyst for direct asymmetric aldol reaction in water

Wenshan Zhaoa, Chengke Qua, Lili Yanga, Yuanchen Cuib   

  1. a College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, Henan, China;
    b Key Laboratory of Ministry of Education for Special Functional Materials, Henan University, Kaifeng 475004, Henan, China
  • Received:2014-09-04 Revised:2014-10-10 Online:2015-02-14 Published:2015-02-14

Abstract:

Chitosan-supported succinic anhydride-cinchonine (CTS-SA-CN) was synthesized via a two-step route with succinic anhydride as the linker. The catalyst was used to promote the direct asymmetric aldol reaction between cyclohexanone and a variety of aromatic aldehydes in aqueous medium. Aldol adducts were obtained in excellent yields (up to 99%) and good enantioselectivities (up to 96% ee). The CTS-SA-CN catalyst was successfully recycled simply by filtration after use, and was reused 5 times without any significant loss of activity.

Key words: Chitosan, Cinchonine, Supported catalyst, Direct asymmetric aldol reaction