Issue 34, 2020, Issue in Progress

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
26 Mar 2020
Accepted
19 May 2020
First published
27 May 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 20264-20271

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

T. K. Beng, V. Shearer, R. Davey and I. Redman, RSC Adv., 2020, 10, 20264 DOI: 10.1039/D0RA03726E

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