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Asymmetric Brønsted acid catalysis with chiral carboxylic acids

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Abstract

Chiral Brønsted acids have found widespread applications as organocatalysts. Weakly acidic species such as diols and (thio)ureas, typically classified as hydrogen bonding catalysts, as well as stronger phosphoric acids, have proven to be highly effective in catalyzing a wide range of asymmetric transformations. In contrast, the use of chiral carboxylic acids as Brønsted acid catalysts is much less developed but has recently garnered increased attention. Given that their pKa's generally lie between those of typical hydrogen bond donors and chiral phosphoric acids, chiral carboxylic acids provide the opportunity to activate a different set of substrates requiring intermediate catalyst acidity. In addition, by taking advantage of judicious catalyst design, the acidity of carboxylic acids can be modulated, for instance by stabilizing the corresponding carboxylate counterion. This review provides an overview of this field, with the aim of highlighting both catalyst design and synthetic applications.

Graphical abstract: Asymmetric Brønsted acid catalysis with chiral carboxylic acids

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Publication details

The article was received on 21 Mar 2016 and first published on 21 Jul 2017


Article type: Review Article
DOI: 10.1039/C6CS00239K
Citation: Chem. Soc. Rev., 2017, Advance Article
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    Asymmetric Brønsted acid catalysis with chiral carboxylic acids

    C. Min and D. Seidel, Chem. Soc. Rev., 2017, Advance Article , DOI: 10.1039/C6CS00239K

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