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  Activation of Carboxylic Acids in Asymmetric Organocatalysis

Monaco, M. R., Poladura, B., Diaz de Los Bernardos, M., Leutzsch, M., Goddard, R., & List, B. (2014). Activation of Carboxylic Acids in Asymmetric Organocatalysis. Angewandte Chemie International Edition, 53(27), 7063-7067. doi:10.1002/anie.201400169.

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 Creators:
Monaco, Mattia Ricardo1, Author              
Poladura, Belén1, Author              
Diaz de Los Bernardos, Miriam1, Author              
Leutzsch, Markus1, Author              
Goddard, Richard2, Author              
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Free keywords: amino alcohols; aziridines; carboxylic acids; organocatalysis; self-assembly
 Abstract: Organocatalysis, catalysis using small organic molecules, has recently evolved into a general approach for asymmetric synthesis, complementing both metal catalysis and biocatalysis.[1] Its success relies to a large extent upon the introduction of novel and generic activation modes.[2] Remarkably though, while carboxylic acids have been used as catalyst directing groups in supramolecular transition-metal catalysis,[3] a general and well-defined activation mode for this useful and abundant substance class is still lacking. Herein we propose the heterodimeric association of carboxylic acids with chiral phosphoric acid catalysts as a new activation principle for organocatalysis. This self-assembly increases both the acidity of the phosphoric acid catalyst and the reactivity of the carboxylic acid. To illustrate this principle, we apply our concept in a general and highly enantioselective catalytic aziridine-opening reaction with carboxylic acids as nucleophiles.

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Language(s): eng - English
 Dates: 2014-01-072014-05-302014-07-01
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201400169
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 53 (27) Sequence Number: - Start / End Page: 7063 - 7067 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851