Journal
SYNTHESIS-STUTTGART
Volume 44, Issue 15, Pages 2295-2309Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0031-1289788
Keywords
N-heterocyclic carbene; azolium enolate; organocatalysis; ketene; alpha-functionalised aldehydes; Enals; activated esters
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Funding
- Royal Society
- EPSRC
- AstraZeneca
- European Research Council under the European Union [279850]
- European Research Council (ERC) [279850] Funding Source: European Research Council (ERC)
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Organocatalysis represents a synthetic paradigm that has grown exponentially in popularity over the last decade, arguably becoming one of the most desired synthetic methods for the creation of enantiomerically enriched products. Within this field the use of N-heterocyclic carbenes (NHCs) has seen appreciable research activity with the realisation of many novel reaction types. This review provides a comprehensive account of recent advances in the generation and reactivity of azolium enolates with exclusive focus on those processes rendered asymmetric through the use of chiral NHCs. 1 Introduction: NHCs in Organocatalysis 1.1 Azolium Enolates 2 Azolium Enolate Generation via Ketenes 2.1 Asymmetric Formal [2+2] Cycloadditions 2.2 Asymmetric Formal [3+2] Cycloadditions 2.3 Asymmetric Formal [4+2] Cycloadditions 2.4 Asymmetric Protonation and Halogenation 3 Azolium Enolate Generation via alpha-Functionalised Aldehydes 4 Azolium Enolate Generation via Enals 5 Activated Esters as Azolium Enolate Precursors 6 Conclusions and Outlook
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