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Metalloradical activation of α-formyldiazoacetates for the catalytic asymmetric radical cyclopropanation of alkenes

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Abstract

For the first time, α-formyldiazoacetates have been successfully applied for the asymmetric cyclopropanation of alkenes via Co(II)-based metalloradical catalysis. The cobalt(II) complex of the D2-symmetric chiral amidoporphyrin [Co(3,5-DitBu-ChenPhyrin)] is an effective metalloradical catalyst that can activate α-formyldiazoacetates to cyclopropanate both aromatic and aliphatic olefins with varied electronic properties, affording the synthetically useful 1,1-cyclopropaneformylesters in high yields with both high diastereo- and enantioselectivity.

Graphical abstract: Metalloradical activation of α-formyldiazoacetates for the catalytic asymmetric radical cyclopropanation of alkenes

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Publication details

The article was received on 12 Feb 2017, accepted on 27 Mar 2017 and first published on 31 Mar 2017


Article type: Edge Article
DOI: 10.1039/C7SC00658F
Citation: Chem. Sci., 2017, Advance Article
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    Metalloradical activation of α-formyldiazoacetates for the catalytic asymmetric radical cyclopropanation of alkenes

    X. Xu, Y. Wang, X. Cui, L. Wojtas and X. P. Zhang, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC00658F

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