Abstract

The α-hydroxy ketone group, or acyloin, is prevalent in natural products and pharmaceuticals, and the development of efficient methods to install this functional group remains an important synthetic challenge. As a result, several distinct methods for the synthesis of α-hydroxy ketones have been developed. This chapter presents a review of approaches toward this structural motif in which the acyloin is derived from the coupling of two carbonyl units to form a new carbon–carbon σ-bond. This definition encompasses the traditional acyloin condensation, involving the reductive coupling of two aliphatic esters, and recent catalytic approaches that invoke acyl anion intermediates (umpolung reactivity).

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