Asymmetric Radical Cyclopropanation of Alkenes with In Situ-Generated Donor-Substituted Diazo Reagents via Co(II)-Based Metalloradical Catalysis
Document Type
Article
Publication Date
2017
Digital Object Identifier (DOI)
https://doi.org/10.1021/jacs.6b11336
Abstract
Donor-substituted diazo reagents, generated in situ from sulfonyl hydrazones in the presence of base, can serve as suitable radical precursors for Co(II)-based metalloradical catalysis (MRC). The cobalt(II) complex of D2-symmetric chiral porphyrin [Co(3,5-DitBu-Xu(2′-Naph)Phyrin)] is an efficient metalloradical catalyst that is capable of activating different N-arylsulfonyl hydrazones for asymmetric radical cyclopropanation of a broad range of alkenes, affording the corresponding cyclopropanes in high yields with effective control of both diastereo- and enantioselectivity. This Co(II)-based metalloradical system represents the first catalytic protocol that can effectively utilize donor-type diazo reagents for asymmetric olefin cyclopropanation.
Was this content written or created while at USF?
Yes
Citation / Publisher Attribution
Journal of the American Chemical Society, v. 139, issue 3, p. 1049-1052
Scholar Commons Citation
Wang, Yong; Wen, Xin; Cui, Xin; Wojtas, Lukasz; and Zhang, X. Peter, "Asymmetric Radical Cyclopropanation of Alkenes with In Situ-Generated Donor-Substituted Diazo Reagents via Co(II)-Based Metalloradical Catalysis" (2017). Chemistry Faculty Publications. 169.
https://digitalcommons.usf.edu/chm_facpub/169
