Site-selective, catalytic, and diastereoselective sp3 C–H hydroxylation and alkoxylation of vicinally functionalized lactams

Authors

Timothy K. Beng, Central Washington University
Victoria Shearer, Central Washington University
Rachel Davey, Central Washington University
Ivianne Redman, Central Washington University

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.

Comments

This article was originally published Open Access in RSC Advances. The full-text article from the publisher can be found here.

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