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Activation of Carboxylic Acids in Asymmetric Organocatalysis

MPS-Authors
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Monaco,  Mattia Ricardo
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Poladura,  Belén
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Diaz de Los Bernardos,  Miriam
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Leutzsch,  Markus
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Goddard,  Richard
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

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.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0024-4B9F-9
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.