Umpolung von Iminen

Finkbeiner, Peter; Nachtsheim, Boris J.

doi:10.1002/nadc.201590367

Nachr Chem

2015

DOI: 10.1002/nadc.201590367

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Umpolung von Iminen

Peter Finkbeiner¹,

Boris J. Nachtsheim²

Abstract: Mit neuen Synthesemethoden lassen sich Imine mit Elektrophilen am Kohlenstoff funktionalisieren.

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Cited by 3 publications

References 12 publications

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Enantioselective N‐Heterocyclic Carbene Catalysis that Exploits Imine Umpolung

et al. 2019

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The catalytic umpolung of imines remains an underdeveloped approach to reaction discovery. Herein we report an enantioselective aza-Stetter reaction that proceeds via imine umpolung using N-heterocyclic carbene catalysis. The reaction proceeds with high levels of enantioselectivity (all ≥96:4 er) and good generality (21 examples). Mechanistic studies are reported and are consistent with turnover limiting addition of the NHC to the imine.

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Enantioselective N‐Heterocyclic Carbene Catalysis that Exploits Imine Umpolung

et al. 2019

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Enantioselective N‐Heterocyclic Carbene Catalysis that Exploits Imine Umpolung

et al. 2019

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The catalytic umpolung of imines remains an underdeveloped approach to reaction discovery.H erein we report an enantioselective aza-Stetter reaction that proceeds via imine umpolung using N-heterocyclic carbene catalysis.T he reaction proceeds with high levels of enantioselectivity (all ! 96:4 er) and good generality (21 examples). Mechanistic studies are reported and are consistent with turnover-limiting addition of the NHC to the imine. Figure 1. Previously and this work.

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One Amine–3 Tasks: Reductive Coupling of Imines with Olefins in Batch and Flow

Lefebvre

Porta

Millet

et al. 2020

Chemistry A European J

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Owing to their wide range of biological properties, g-aminobutyric acid derivatives (GABA) have been extensively studied and foundn oteworthy industrial applications. However,a tom-economical and efficient processes for their production are scarce and would greatly benefit from further investigations.H erein, we demonstrate that an iridiumbased photocatalyst promotes the direct reductive cross-coupling of imines with olefins upon irradiation with visible light to give GABA derivatives in good yields and selectivities. We also stress the enablingt riple role of tributylamine additivei nt his process, discuss the advantages of strategies based on proton-coupled electron transfer (PCET) and demonstrate the scale-up of this reaction in continuous flow.

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Umpolung von Iminen

Abstract: Mit neuen Synthesemethoden lassen sich Imine mit Elektrophilen am Kohlenstoff funktionalisieren.

Cited by 3 publications

References 12 publications

Enantioselective N‐Heterocyclic Carbene Catalysis that Exploits Imine Umpolung

Enantioselective N‐Heterocyclic Carbene Catalysis that Exploits Imine Umpolung

Enantioselective N‐Heterocyclic Carbene Catalysis that Exploits Imine Umpolung

One Amine–3 Tasks: Reductive Coupling of Imines with Olefins in Batch and Flow

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