Metalloradical Activation of Α-formyldiazoacetates for the Catalytic Asymmetric Radical Cyclopropanation of Alkenes

Authors

Xue Xu, University of South Florida
Yong Wang, Boston College
Xin Cui, University of South Florida
Lukasz Wojtas, University of South FloridaFollow
X. Peter Zhang, Boston College

Document Type

Article

Publication Date

2017

Digital Object Identifier (DOI)

https://doi.org/10.1039/C7SC00658F

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-Di^tBu-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.

Rights Information

This work is licensed under a Creative Commons Attribution 3.0 License.

Was this content written or created while at USF?

Yes

Citation / Publisher Attribution

Chemical Science, v. 8, issue 6, p. 4347-4351

Scholar Commons Citation

Xu, Xue; Wang, Yong; Cui, Xin; Wojtas, Lukasz; and Zhang, X. Peter, "Metalloradical Activation of Α-formyldiazoacetates for the Catalytic Asymmetric Radical Cyclopropanation of Alkenes" (2017). Chemistry Faculty Publications. 106.
https://digitalcommons.usf.edu/chm_facpub/106