Enantioselective Radical Cyclization for Construction of 5-Membered Ring Structures by Metalloradical C–H Alkylation
Document Type
Article
Publication Date
3-2018
Digital Object Identifier (DOI)
https://doi.org/10.1021/jacs.8b01662
Abstract
Radical cyclization represents a powerful strategy for construction of ring structures. Traditional radical cyclization, which is based on radical addition as the key step, necessitates the use of unsaturated substrates. Guided by the concept of metalloradical catalysis, a different mode of radical cyclization that can employ saturated C−H substrates is demonstrated through the development of a Co(II)-based system for catalytic activation of aliphatic diazo compounds for enantioselective radical alkylation of various C(sp3)−H bonds. It allows for efficient construction of chiral pyrrolidines and other valuable 5-membered cyclic compounds. This alternative strategy of radical cyclization provides a new retrosynthetic paradigm to prepare five-membered cyclic molecules from readily available open-chain aldehydes through the union of C−H and C=O elements for C−C bond formation.
Was this content written or created while at USF?
Yes
Citation / Publisher Attribution
Journal of the American Chemical Society, v. 140, issue 14, p. 4792-4796
Scholar Commons Citation
Wang, Yong; Wen, Xin; Cui, Xin; and Zhang, X. P., "Enantioselective Radical Cyclization for Construction of 5-Membered Ring Structures by Metalloradical C–H Alkylation" (2018). Chemistry Faculty Publications. 84.
https://digitalcommons.usf.edu/chm_facpub/84
