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Chemoenzymatic preparation of optically active cyclic 4-hydroxy-acylaziridines

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Abstract

(x + 1)-Hydroxyazabicyclo[x.1.0]alkane-2-ones are useful intermediates for organic synthesis. A method for the preparation of these bicyclic 4-hydroxy-acylaziridines in optically active form is described. Stereoselective aziridination of racemic protected 4-hydroxycycloenones followed by enzymatic resolution with Novozym 435 (CAL-B) afforded the chiral hydroxyaziridines in good yields and enantiomeric excess (up to 99%). The described method is simple, reproducible and scalable. A stereoselective tandem elimination followed by 1,4-addition on a cyclopentanone is also described.

Graphical abstract: Chemoenzymatic preparation of optically active cyclic 4-hydroxy-acylaziridines

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Publication details

The article was received on 31 Mar 2017, accepted on 16 May 2017 and first published on 17 May 2017


Article type: Research Article
DOI: 10.1039/C7QO00254H
Citation: Org. Chem. Front., 2017, Advance Article
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    Chemoenzymatic preparation of optically active cyclic 4-hydroxy-acylaziridines

    S. Silva and C. D. Maycock, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00254H

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