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

2007, Volume 1, Issue 3

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Frontiers of Chemical Science and Engineering >> 2007, Volume 1, Issue 3 doi: 10.1007/s11705-007-0045-1

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

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

Available online: 2007-09-05

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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 enantioselectivity 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 70ºC and reaction time 4 h, enantiomer excess (ee) of ()-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 ()-4-methyl-2-pentanol and conversion 4-methyl-2-pentanone amounted to 50.2% and 25.5%, respectively.

Keywords

asymmetric transfer ; enantioselectivity ; Fe-CS/SBA-15 ; aliphatic ; aromatic

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