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Issue 12, 2018
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Two stereocentered HKR of anti-β,β′-diphenylpropanoxirane and anti-3-phenylethyloxiranes catalysed by Co(III)(salen)-OAc complex: enantioselective synthesis of (+)-sertraline and (+)-naproxen

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Abstract

The Co(III)(salen)OAc-catalyzed two stereocentered hydrolytic kinetic resolution (HKR) of anti-β,β′-diphenylmethyloxirane and anti-3-phenylethyloxiranes affords the corresponding anti-1,2-diols and oxiranes in high enantiomeric excess. The synthetic potential of this methodology is demonstrated by the enantioselective synthesis of (+)-sertraline, an antidepressant drug, and (+)-naproxen, an anti-inflammatory drug.

Graphical abstract: Two stereocentered HKR of anti-β,β′-diphenylpropanoxirane and anti-3-phenylethyloxiranes catalysed by Co(iii)(salen)-OAc complex: enantioselective synthesis of (+)-sertraline and (+)-naproxen

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Publication details

The article was received on 03 Apr 2018, accepted on 11 May 2018 and first published on 14 May 2018


Article type: Paper
DOI: 10.1039/C8NJ01616J
Citation: New J. Chem., 2018,42, 10414-10420
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    Two stereocentered HKR of anti-β,β′-diphenylpropanoxirane and anti-3-phenylethyloxiranes catalysed by Co(III)(salen)-OAc complex: enantioselective synthesis of (+)-sertraline and (+)-naproxen

    R. B. Kamble, D. Devalankar and G. Suryavanshi, New J. Chem., 2018, 42, 10414
    DOI: 10.1039/C8NJ01616J

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