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Literature DB >> 15600319

Probing the active catalyst in product-accelerated proline-mediated reactions.

Hiroshi Iwamura¹, David H Wells, Suju P Mathew, Martin Klussmann, Alan Armstrong, Donna G Blackmond.

Abstract

A new catalytic cycle involving only soluble proline complexes or adducts is proposed for the reactions in eq 1 based on kinetic observations and molecular modeling studies. This reaction pathway circumventing free proline and incorporating hydrogen-bonded reaction product helps to rationalize the observations of accelerating reaction rate in both the alpha-aminooxylation and alpha-amination reactions.

Entities: Chemical

Mesh：

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Year: 2004 PMID： 15600319 DOI： 10.1021/ja0444177

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

8 in total

Review 1. Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

Authors: Paul Ha-Yeon Cheong; Claude Y Legault; Joann M Um; Nihan Çelebi-Ölçüm; K N Houk
Journal: Chem Rev Date: 2011-06-28 Impact factor: 60.622

2. Bronsted acid catalysis of achiral enamine for regio- and enantioselective nitroso aldol synthesis.

Authors: Norie Momiyama; Hisashi Yamamoto
Journal: J Am Chem Soc Date: 2005-02-02 Impact factor: 15.419

3. A quantitative approach to nucleophilic organocatalysis.

Authors: Herbert Mayr; Sami Lakhdar; Biplab Maji; Armin R Ofial
Journal: Beilstein J Org Chem Date: 2012-09-05 Impact factor: 2.883

4. Single particle tracking-based reaction progress kinetic analysis reveals a series of molecular mechanisms of cetuximab-induced EGFR processes in a single living cell.

Authors: Do-Hyeon Kim; Dong-Kyun Kim; Kai Zhou; Soyeon Park; Yonghoon Kwon; Min Gyu Jeong; Nam Ki Lee; Sung Ho Ryu
Journal: Chem Sci Date: 2017-04-24 Impact factor: 9.825

Probing the active catalyst in product-accelerated proline-mediated reactions.

Review 1. Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

2. Bronsted acid catalysis of achiral enamine for regio- and enantioselective nitroso aldol synthesis.

3. A quantitative approach to nucleophilic organocatalysis.

4. Single particle tracking-based reaction progress kinetic analysis reveals a series of molecular mechanisms of cetuximab-induced EGFR processes in a single living cell.

Review 5. Organocatalyzed asymmetric alpha-oxidation, alpha-aminoxylation and alpha-amination of carbonyl compounds.

6. Proline-catalysed amination reactions in cyclic carbonate solvents.

7. Unusually high α-proton acidity of prolyl residues in cyclic peptides.

8. A new charge-tagged proline-based organocatalyst for mechanistic studies using electrospray mass spectrometry.