α-amination reaction of different ketones mediated by carbohydrate Cu2+ complexes

Rossi, L.; Krapacher, Claudio R.; Granados, Alejandro M.

doi:10.1016/j.mcat.2020.111058

Cited by 3 publications

(1 citation statement)

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“…[31][32][33][34][35][36][37][38] In nucleophilic amination involving umpolung of carbonyl compounds, -oxidation or -halogenation of the carbonyl fragment allows coupling to an amine, although these methods were until recently limited to construction of tertiary amines (Figure 1B). [39][40][41][42][43][44][45][46][47][48][49][50] A consequence of umpolung-based approaches is the necessity for multiple steps to effect the necessary polarity reversal of one reaction component.…”

Section: Introductionmentioning

confidence: 99%

Direct alpha-Amination of Amides and Lactams Enabled by the (3+2) Vinyl Azide-Enolate Cycloaddition Manifold

Bell-Tyrer

Hume

Grant

et al. 2022

Preprint

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Direct alpha-amination of carbonyl compounds remains an important yet synthetically challenging transformation. Here we report a solution for direct alpha-amination of amides and lactams, identified through fundamental exploration of (3+2) vinyl azide-enolate cycloaddition chemistry. Initial cycloadducts undergo rearrangement via 1,2-N-migration to afford imine intermediates that are readily converted to the target alpha-amino amides or lactams. The sequence requires no pre-functionalisation, can be performed on a range of substrates, including compound classes unsuccessful using reported methods, and delivers primary or secondary alpha-amines. This work highlights the diversity and synthetic potential of the rapidly expanding (3+2) azide-enolate cycloaddition manifold.

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Section: Introductionmentioning

confidence: 99%

Direct alpha-Amination of Amides and Lactams Enabled by the (3+2) Vinyl Azide-Enolate Cycloaddition Manifold

Bell-Tyrer

Hume

Grant

et al. 2022

Preprint

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Comparative green analysis between different catalytic methodologies used in stereoselective reduction reaction of acetophenone

et al. 2021

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Research Progress of Carbonyl α-Position Amination

Wu,

Chen,

Peng

et al. 2023

Chinese Journal of Organic Chemistry

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Amino carbonyl derivatives are an important class of molecular backbones found in many pharmaceuticals and natural product molecules, meanwhile, they are also an essential kind of intermediates for the synthesis of many organic molecules. To develop simple and efficient method for the synthesis of structurally diversity α-amino carbonyl derivatives of great importance, the amination reactions of carbonyl α-position hydrocarbon bond in recent decades are classified and summarized based on the different activation patterns experienced by the reactions. These reactions are mainly divided into four categories: electrophilic amination, oxidative amination, halide mediated amination, and electrochemical amination.

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α-amination reaction of different ketones mediated by carbohydrate Cu2+ complexes

Cited by 3 publications

References 31 publications

Direct alpha-Amination of Amides and Lactams Enabled by the (3+2) Vinyl Azide-Enolate Cycloaddition Manifold

Direct alpha-Amination of Amides and Lactams Enabled by the (3+2) Vinyl Azide-Enolate Cycloaddition Manifold

Comparative green analysis between different catalytic methodologies used in stereoselective reduction reaction of acetophenone

Research Progress of Carbonyl α-Position Amination

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