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Issue 7, 2015
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One-pot relay reduction–isomerization of β-trifluoromethylated-α,β-unsaturated ketones to chiral β-trifluoromethylated saturated ketones over combined catalysts in aqueous medium

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Abstract

Despite great achievements obtained in tandem reactions, a solution for the incompatible nature of bimetal complexes participating in a multi-step catalytic process is still an unmet challenge. Herein, we utilize a functionalized periodic mesoporous organosilica with well-defined single-site chiral organoruthenium active centers in its ordered dimensional-hexagonal mesopores as a heterogeneous catalyst, and combine it with [RuCl2(PPh3)3] to enable an efficient one-pot relay reduction–isomerization from achiral β-trifluoromethylated-α,β-unsaturated ketones to chiral β-trifluoromethylated saturated ketones in water with up to 97% ee and 100% enantiospecificity, supplying a gap in their incompatibility. Furthermore, the heterogeneous catalyst can be recovered conveniently and reused repeatedly at least eight times without loss of reactivity in the enantioselective reduction of 4,4,4-trifluoro-1,3-diphenylbut-2-enone, showing it to be particularly attractive in the practice of organic synthesis in an environmentally friendly manner.

Graphical abstract: One-pot relay reduction–isomerization of β-trifluoromethylated-α,β-unsaturated ketones to chiral β-trifluoromethylated saturated ketones over combined catalysts in aqueous medium

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Publication details

The article was received on 03 Mar 2015, accepted on 15 May 2015 and first published on 18 May 2015


Article type: Paper
DOI: 10.1039/C5GC00479A
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Green Chem., 2015,17, 3916-3922

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    One-pot relay reduction–isomerization of β-trifluoromethylated-α,β-unsaturated ketones to chiral β-trifluoromethylated saturated ketones over combined catalysts in aqueous medium

    X. Xia, M. Wu, R. Jin, T. Cheng and G. Liu, Green Chem., 2015, 17, 3916
    DOI: 10.1039/C5GC00479A

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