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.

Original languageEnglish
Pages (from-to)1620-1623
Number of pages4
JournalOrganic Chemistry Frontiers
Volume4
Issue number8
DOIs
Publication statusPublished - 1 Aug 2017

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