Issue 6, 2017

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2017,8, 4347-4351

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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