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Literature DB >> 23039069

One-pot catalytic enantioselective synthesis of tetrahydropyridines via a nitro-Mannich/hydroamination cascade.

David M Barber¹, Hitesh J Sanganee, Darren J Dixon.

Abstract

The highly enantioselective preparation of synthetically useful tetrahydropyridine derivatives employing a one-pot nitro-Mannich/hydroamination cascade is reported. This approach utilizes an asymmetric organocatalytic nitro-Mannich reaction followed by a gold-catalyzed alkyne hydroamination/isomerization sequence that yields the desired tetrahydropyridines in good yields and high diastereo- and enantioselectivities.

Entities: Chemical

Mesh：

Substances：
Nitro Compounds
Pyridines

Year: 2012 PMID： 23039069 DOI： 10.1021/ol302459c

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

6 in total

1. Click-Engineered, Bioresponsive, and Versatile Particle-Protein-Dye System.

Authors: Mary K Burdette; Ragini Jenkins; Yuriy P Bandera; Haley Jones; Isabell K Foulger; Ashley Dickey; Anna-Liisa Nieminen; Stephen H Foulger
Journal: ACS Appl Bio Mater Date: 2019-07-01

2. Asymmetric synthesis of tetrahydropyridines via an organocatalytic one-pot multicomponent Michael/aza-Henry/cyclization triple domino reaction.

Authors: Marcus Blümel; Pankaj Chauhan; Robert Hahn; Gerhard Raabe; Dieter Enders
Journal: Org Lett Date: 2014-11-07 Impact factor: 6.005

3. One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis.

Authors: David M Barber; Andrej Duriš; Amber L Thompson; Hitesh J Sanganee; Darren J Dixon
Journal: ACS Catal Date: 2014-01-06 Impact factor: 13.084

One-pot catalytic enantioselective synthesis of tetrahydropyridines via a nitro-Mannich/hydroamination cascade.

1. Click-Engineered, Bioresponsive, and Versatile Particle-Protein-Dye System.

2. Asymmetric synthesis of tetrahydropyridines via an organocatalytic one-pot multicomponent Michael/aza-Henry/cyclization triple domino reaction.

3. One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis.

4. Iridium-catalyzed reductive nitro-Mannich cyclization.

5. Gold and BINOL-phosphoric acid catalyzed enantioselective hydroamination/N-sulfonyliminium cyclization cascade.

6. Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis.