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Bae, Han Yong
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Cinchona-based Sulfonamide Organocatalysts: Concept, Scope, and Practical Applications

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Title
Cinchona-based Sulfonamide Organocatalysts: Concept, Scope, and Practical Applications
Author
Bae, Han YongSong, Choong Eui
Keywords
Asymmetric catalysis;  Cinchona-based sulfonamide;  Textile organocatalysis;  Desymmetrization;  Aldol reaction
Issue Date
201406
Publisher
KOREAN CHEMICAL SOC
Citation
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.35, no.6, pp.1590 - 1600
Abstract
Cinchona-based bifunctional catalysts have been extensively employed in the field of organocatalysis due to the incorporation of both hydrogen-bonding acceptors (quinuclidine) and hydrogen-bonding donors (e.g., alcohol, amide, (thio)urea and squaramide) in the molecule, which can simultaneously activate nucleophiles and electrophiles, respectively. Among them, cinchona-derived (thio)urea and squaramide catalysts have shown remarkable application potential by using their bifurcated hydrogen bonding donors in activating electrophilic carbonyls and imines. However, due to their bifunctional nature, they tend to aggregate via inter- and intramolecular acid-base interactions under certain conditions, which can lead to a decrease in the enantioselectivity of the reaction. To overcome this self-aggregation problem of bifunctional organocatalysts, we have successfully developed a series of sulfonamide-based organocatalysts, which do not aggregate under conventional reaction conditions. Herein, we summarize the recent applications of our cinchona-derived sulfonamide organocatalysts in highly enantioselective methanolytic desymmetrization and decarboxylative aldol reactions. Immobilization of sulfonamide-based catalysts onto solid supports allowed for unprecedented practical applications in the synthesis of valuable bioactive synthons with excellent enantioselectivities.
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DOI
http://dx.doi.org/10.5012/bkcs.2014.35.6.1590
ISSN
0253-2964
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