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Issue 2, 2009
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Chemo-enzymatic synthesis of N-alkyloxaziridines mediated by lipases and urea-hydrogen peroxide

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Abstract

Chemo-enzymatic oxidation of various N-alkylimines mediated by lipases produced the corresponding E- or a mixture of E- and Z-N-oxaziridines with moderate to very high yields (>99%) and good to excellent selectivities (70–100%) within 30 min to 6 h in various organic solvents at room temperature (25 °C) with urea-hydrogen peroxide (UHP) or aqueous hydrogen peroxide (AHP). The E/Z isomer ratio was critically dependent on the stereo-electronic nature of the substituents in the N-alkylimines. The influence of organic solvents, acyl donor and lipase mass was evaluated in these reactions.

Graphical abstract: Chemo-enzymatic synthesis of N-alkyloxaziridines mediated by lipases and urea-hydrogen peroxide

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Supplementary files

Article information


Submitted
29 Sep 2008
Accepted
24 Oct 2008
First published
19 Nov 2008

Green Chem., 2009,11, 209-214
Article type
Paper

Chemo-enzymatic synthesis of N-alkyloxaziridines mediated by lipases and urea-hydrogen peroxide

T. B. Bitencourt and M. da Graça Nascimento, Green Chem., 2009, 11, 209
DOI: 10.1039/B816955A

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