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Issue 6, 2017
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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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Article information


Submitted
12 Feb 2017
Accepted
27 Mar 2017
First published
31 Mar 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 4347-4351
Article type
Edge Article

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, 8, 4347
DOI: 10.1039/C7SC00658F

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