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Literature DB >> 24311406

Hydrogen-bonding in aminocatalysis: from proline and beyond.

Lukasz Albrecht¹, Hao Jiang, Karl Anker Jørgensen.

Abstract

This Concept article summarizes recent progress in the field of hydrogen-bonding aminocatalysis using proline-derived systems. The aminocatalysts available in the literature are categorized by the incorporated hydrogen-bonding scaffold and its mode of recognition. Both mono- and double-hydrogen-bonding motifs are discussed and examples of their application in asymmetric synthesis are given.

Entities: Chemical

Keywords: aminocatalysis; asymmetric catalysis; bifunctional catalysis; hydrogen bonds; proline; stereoselective synthesis

Mesh：

Substances：
Pyrrolidines
Proline

Year: 2013 PMID： 24311406 DOI： 10.1002/chem.201303982

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

5 in total

5. (2S,4R)-4-hydroxyproline(4-nitrobenzoate): strong induction of stereoelectronic effects via a readily synthesized proline derivative. Crystallographic observation of a correlation between torsion angle and bond length in a hyperconjugative interaction.

Authors: Anil K Pandey; Glenn P A Yap; Neal J Zondlo
Journal: J Org Chem Date: 2014-04-18 Impact factor: 4.354

5 in total

Hydrogen-bonding in aminocatalysis: from proline and beyond.

1. Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination.

2. Old tricks, new dogs: organocatalytic dienamine activation of α,β-unsaturated aldehydes.

3. Development of bifunctional organocatalysts and application to asymmetric total synthesis of naucleofficine I and II.

4. Dynamic Stereochemistry of a Biphenyl-Bisprolineamide Model Catalyst and its Imidazolidinone Intermediates.

5. (2S,4R)-4-hydroxyproline(4-nitrobenzoate): strong induction of stereoelectronic effects via a readily synthesized proline derivative. Crystallographic observation of a correlation between torsion angle and bond length in a hyperconjugative interaction.