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).
Original language | English (US) |
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Title of host publication | Comprehensive Organic Synthesis |
Subtitle of host publication | Second Edition |
Publisher | Elsevier Ltd |
Pages | 621-655 |
Number of pages | 35 |
Volume | 3 |
ISBN (Print) | 9780080977430 |
DOIs | |
State | Published - Feb 2014 |
Keywords
- Acyl anion equivalent
- Acyloin
- Benzoin
- N-heterocyclic carbene
- Organocatalysis
- Reductive coupling
- Umpolung
- α-Hydroxy ketone
ASJC Scopus subject areas
- Chemistry(all)
- Chemical Engineering(all)