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Asymmetric transfer hydrogenation of prochiral ketone catalyzed over Fe-CS/SBA-15 catalyst

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Abstract

A heterogeneous chiral catalyst Fe(III)-CS (chitosan) complex/mesoporous molecular sieve SBA-15 (Santa Barbara Amorphous) was prepared. The asymmetric transfer hydrogenations of prochiral acetophenone and 4-methyl-2-pentanone to corresponding chiral alcohols were carried out on Fe-CS/SBA-15 at atmosphere pressure using 2-propanol as hydrogen donor. Effects of Fe content in catalyst, reaction temperature, reaction time and promoter KOH concentration on the conversion of substrates and enantio-selectivity were investigated. Fe-CS/SBA-15 with 2.2% mass fraction Fe exhibits considerable enantioselectivity and catalytic activity for the asymmetric transfer hydrogenations of aromatic ketone and aliphatic ketone. Under optimal reaction conditions: KOH concentration 0.03 mol/L, reaction temperature 70°C and reaction time 4 h, enantiomer excess (ee) of (R)-1-phenylethanol and conversion of acetophenone can reach 87.4% and 27.7%, respectively. Under the above KOH concentration and reaction temperature and reaction time of 8 h, the ee of (R)-4-methyl-2-pentanol and conversion 4-methyl-2-pentanone amounted to 50.2% and 25.5%, respectively.

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Authors and Affiliations

  1. Key Laboratory of Energy Resources and Chemical Engineering, Ningxia University, Yinchuan, 750021, China

    Xue Ping & Wu Tao

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  1. Xue Ping
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  2. Wu Tao
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Correspondence to Xue Ping.

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Translated from Petrochemical Technology, 2006, 35(9): 858–862 [译自: 石油化工]

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Xue, P., Wu, T. Asymmetric transfer hydrogenation of prochiral ketone catalyzed over Fe-CS/SBA-15 catalyst. Front. Chem. Eng. China 1, 251–255 (2007). https://doi.org/10.1007/s11705-007-0045-1

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  • DOI: https://doi.org/10.1007/s11705-007-0045-1

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