Oxidative α-acyloxylation of acetals with cyclic diacyl peroxides?

Organic Chemistry Frontiers Pub Date: 2021-04-12 DOI: 10.1039/D1QO00494H

Abstract

An acetal fragment is a well-known protective group which does not activate the neighboring α-position. Selective functionalization of the non-activated acetal α-position with formal retaining of the acetal fragment was realized using cyclic diacyl peroxides. The discovered oxidative C–O coupling of cyclic diacyl peroxides with acetals leads to α-acyloxy acetals with a free carboxylic acid group in 42–85% yields. The reaction probably proceeds via in situ enol ether formation, oxidative [5 + 2] cycloaddition, and the recovery of the acetal fragment.

Graphical abstract: Oxidative α-acyloxylation of acetals with cyclic diacyl peroxides
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