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.

SUBMITTER: Beng TK 

PROVIDER: S-EPMC9054119 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature