e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Redox-Neutral α-Cyanation of Amines

L Ma, W Chen, D Seidel

Index: Ma, Longle; Chen, Weijie; Seidel, Daniel Journal of the American Chemical Society, 2012 , vol. 134, # 37 p. 15305 - 15308

Full Text: HTML

Citation Number: 46

Abstract

α-Aminonitriles inaccessible by traditional Strecker chemistry are obtained in redox-neutral fashion by direct amine α-cyanation/N-alkylation or alternatively, α-aminonitrile isomerization. These unprecedented transformations are catalyzed by simple carboxylic acids.

Piperidine Structure

Mandelonitrile Structure

~%

1-Piperidineacetonitrile,a-phenyl- Structure

1-Piperidineace...

1-benzylpiperidine-2-carbonitrile Structure

1-benzylpiperid...

Benzaldehyde Structure

~%

1-Piperidineacetonitrile,a-phenyl- Structure

1-Piperidineace...

1-benzylpiperidine-2-carbonitrile Structure

1-benzylpiperid...

Pyrrolidine Structure

Mandelonitrile Structure

~%

2-phenyl-2-pyrrolidin-1-ylacetonitrile Structure

2-phenyl-2-pyrr...

1-benzylpyrrolidine-2-carbonitrile Structure

1-benzylpyrroli...

Pyrrolidine Structure

Trimethylsilyl cyanide Structure

Trimethylsilyl ...

Benzaldehyde Structure

~%

2-phenyl-2-pyrrolidin-1-ylacetonitrile Structure

2-phenyl-2-pyrr...

Detail

Benzaldehyde Structure

~%

2-phenyl-2-pyrrolidin-1-ylacetonitrile Structure

2-phenyl-2-pyrr...

1-benzylpyrrolidine-2-carbonitrile Structure

1-benzylpyrroli...

Pyrrolidine Structure

Benzeneacetonitrile, a-hydroxy-4-methoxy- Structure

Benzeneacetonit...

~%

1-(4-methoxybenzyl)pyrrolidine-2-carbonitrile Structure

1-(4-methoxyben...

1-Pyrrolidineacetonitrile,a-(4-methoxyphenyl)- Structure

1-Pyrrolidineac...

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

~%

1-(4-methoxybenzyl)pyrrolidine-2-carbonitrile Structure

1-(4-methoxyben...

1-Pyrrolidineacetonitrile,a-(4-methoxyphenyl)- Structure

1-Pyrrolidineac...

2-phenyl-2-pyrrolidin-1-ylacetonitrile Structure

2-phenyl-2-pyrr...

~%

1-benzylpyrrolidine-2-carbonitrile Structure

1-benzylpyrroli...

Pyrrolidine Structure

Mandelonitrile Structure

~%

2-phenyl-2-pyrrolidin-1-ylacetonitrile Structure

2-phenyl-2-pyrr...

1-benzylpyrrolidine-2-carbonitrile Structure

1-benzylpyrroli...

Pyrrolidine Structure

Trimethylsilyl cyanide Structure

Trimethylsilyl ...

Benzaldehyde Structure

~%

2-phenyl-2-pyrrolidin-1-ylacetonitrile Structure

2-phenyl-2-pyrr...

Detail

Benzaldehyde Structure

~%

2-phenyl-2-pyrrolidin-1-ylacetonitrile Structure

2-phenyl-2-pyrr...

1-benzylpyrrolidine-2-carbonitrile Structure

1-benzylpyrroli...

Azepane Structure

Mandelonitrile Structure

~%

1-benzylazepane-2-carbonitrile Structure

1-benzylazepane...

azepan-1-yl(phenyl)acetonitrile(SALTDATA: FREE) Structure

azepan-1-yl(phe...

Benzaldehyde Structure

~%

1-benzylazepane-2-carbonitrile Structure

1-benzylazepane...

azepan-1-yl(phenyl)acetonitrile(SALTDATA: FREE) Structure

azepan-1-yl(phe...

1,2,3,4-Tetrahydroisoquinoline Structure

1,2,3,4-Tetrahy...

Mandelonitrile Structure

~%

N/A Structure

2-(3,4-dihydroisoquinolin-2(1H)-yl)-2-phenylacetonitrile Structure

2-(3,4-dihydroi...

Detail

Piperidine Structure

Mandelonitrile Structure

~%

1-Piperidineacetonitrile,a-phenyl- Structure

1-Piperidineace...

1-benzylpiperidine-2-carbonitrile Structure

1-benzylpiperid...

Benzaldehyde Structure

~%

1-Piperidineacetonitrile,a-phenyl- Structure

1-Piperidineace...

1-benzylpiperidine-2-carbonitrile Structure

1-benzylpiperid...

Cyclization via Carbolithiation of α-Amino Alkyllithium Reag...

[Bahde, Robert J.; Rychnovsky, Scott D. Organic Letters, 2008 , vol. 10, # 18 p. 4017 - 4020]

The decarboxylative strecker reaction

[Das, Deepankar; Richers, Matthew T.; Ma, Longle; Seidel, Daniel Organic Letters, 2011 , vol. 13, # 24 p. 6584 - 6587]

The decarboxylative strecker reaction

[Das, Deepankar; Richers, Matthew T.; Ma, Longle; Seidel, Daniel Organic Letters, 2011 , vol. 13, # 24 p. 6584 - 6587]

A new and practical procedure for the bruylants reaction. Zi...

[Bernardi, Luca; Bonini, Bianca F.; Capito, Elena; Dessole, Gabriella; Fochi, Mariafrancesca; Comes-Franchini, Mauro; Ricci, Alfredo Synlett, 2003 , # 12 p. 1778 - 1782]