Biocatalytic One-Carbon Ring Expansion of Aziridines to Azetidinesvia a Highly Enantioselective [1,2]-Stevens Rearrangement br
- Journal Article
We report enantioselective one-carbon ring expansion of aziridines to make azetidines as a new-to-nature activity ofengineered"carbene transferase"enzymes. A laboratory-evolved variant of cytochrome P450BM3, P411-AzetS, not only exertsunparalleled stereocontrol (99:1 er) over a [1,2]-Stevens rearrangement but also overrides the inherent reactivity of aziridiniumylides, cheletropic extrusion of olefins, to perform a [1,2]-Stevens rearrangement. By controlling the fate of the highly reactiveaziridinium ylide intermediates, these evolvable biocatalysts promote a transformation which cannot currently be performed usingother catalyst classes. Show more
Journal / seriesJournal of the American Chemical Society
Pages / Article No.
PublisherAmerican Chemical Society
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