Document Type
Article
Department or Administrative Unit
Chemistry
Publication Date
5-27-2020
Abstract
The C–H bond functionalization of sp3 carbon centres presents a significant challenge due to the inert nature of hydrocarbons as well as the need to selectively functionalize one of the numerous aliphatic C–H bonds embodied in organic molecules. Here, we describe catalytic, diastereoselective, and site-selective sp3 C–H hydroxylation/alkoxylation protocols featuring dihydroisoquinolones, γ-, and δ-lactams, which bear vicinal stereocenters. The hydroxylation strategy utilizes oxygen, a waste-free oxidant and affords attractive fragments for potential drug discovery. Fe-catalyzed dehydrative coupling of the resulting tertiary alcohols with simple primary alcohols has led to the construction of highly versatile unsymmetrical dialkyl ethers.
Recommended Citation
Beng, T. K., Shearer, V., Davey, R., & Redman, I. (2020). Site-selective, catalytic, and diastereoselective sp3 C–H hydroxylation and alkoxylation of vicinally functionalized lactams. RSC Advances, 10(34), 20264–20271. https://doi.org/10.1039/d0ra03726e
Journal
RSC Advances
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial 3.0 License
Rights
© The Royal Society of Chemistry 2020
Comments
This article was originally published Open Access in RSC Advances. The full-text article from the publisher can be found here.