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Literature DB >> 24470000

Hydrogenative dearomatization of pyridine and an asymmetric aza-Friedel-Crafts alkylation sequence.

Abstract

Highly efficient synthesis of enantiomerically enriched substituted piperidines has been realized via chiral phosphoric acid catalyzed cascade hydrogenative dearomatization of substituted pyridines and aza-Friedel-Crafts reaction in good to excellent yields and enantioselectivity.

Entities: Chemical

Keywords: asymmetric catalysis; heterocycles; organocatalysis; reduction; synthetic methods

Mesh：

Substances：

Year: 2014 PMID： 24470000 DOI： 10.1002/anie.201309876

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

6 in total

1. Evidence for Simultaneous Dearomatization of Two Aromatic Rings under Mild Conditions in Cu(I)-Catalyzed Direct Asymmetric Dearomatization of Pyridine.

Authors: Michael W Gribble; Richard Y Liu; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2020-06-11 Impact factor: 15.419

2. Rapid Construction of (-)-Paroxetine and (-)-Femoxetine via N-Heterocyclic Carbene Catalyzed Homoenolate Addition to Nitroalkenes.

Authors: Nicholas A White; Kerem E Ozboya; Darrin M Flanigan; Tomislav Rovis
Journal: Asian J Org Chem Date: 2014-04 Impact factor: 3.319

Hydrogenative dearomatization of pyridine and an asymmetric aza-Friedel-Crafts alkylation sequence.

1. Evidence for Simultaneous Dearomatization of Two Aromatic Rings under Mild Conditions in Cu(I)-Catalyzed Direct Asymmetric Dearomatization of Pyridine.

2. Rapid Construction of (-)-Paroxetine and (-)-Femoxetine via N-Heterocyclic Carbene Catalyzed Homoenolate Addition to Nitroalkenes.

3. Transition-Metal-Free Reductive Hydroxymethylation of Isoquinolines.

4. Reductive Hydroxymethylation of 4-Heteroarylpyridines.

Review 5. Chiral Phosphoric Acids as Versatile Tools for Organocatalytic Asymmetric Transfer Hydrogenations.

6. Single point activation of pyridines enables reductive hydroxymethylation.