Journal ArticleDOI
Recognition and activation by ureas and thioureas: stereoselective reactions using ureas and thioureas as hydrogen-bonding donors.
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TLDR
Enantioselective reactions catalyzed by urea and thiourea derivatives as general acid catalysts as well as diastereoselectives reactions are described.Abstract:
Hydrogen-bonding interaction plays a crucial role in the molecular recognition and activation processes of various biologically important reactions that are mediated by enzymes and antibodies in living organisms. Recently, it has been shown that a hydrogen-bonding donor can be used as a general acid catalyst for various types of reactions in organic chemistry. In this article, we describe enantioselective reactions catalyzed by urea and thiourea derivatives as general acid catalysts as well as diastereoselective reactions. This perspective provides an overview of this rapidly growing field.read more
Citations
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Asymmetric aminocatalysis--gold rush in organic chemistry.
TL;DR: This Review describes this "Asymmetric Aminocatalysis Gold Rush" and charts the milestones in its development.
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(Thio)urea organocatalysis—What can be learnt from anion recognition?
Zhiguo Zhang,Peter R. Schreiner +1 more
TL;DR: The present critical review outlines the close relationship and mutual interplay between molecular recognition, active site considerations in enzyme catalysis involving anions, and organocatalysis utilizing explicit hydrogen bonding.
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Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts.
TL;DR: Cinchona alkaloid derivatives modified to include a (thio)urea component have emerged in the last three years as readily accessible, robust and tunable bifunctional organocatalysts for a range of synthetically useful transformations.
References
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Encoding and decoding hydrogen-bond patterns of organic compounds
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In the Golden Age of Organocatalysis
Peter I. Dalko,Lionel Moisan +1 more
TL;DR: The diverse examples show that in recent years organocatalysis has developed within organic chemistry into its own subdiscipline, whose "Golden Age" has already dawned.
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Artificial Organic Host Molecules for Anions
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Enantioselective Mannich‐Type Reaction Catalyzed by a Chiral Brønsted Acid
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Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts
TL;DR: Michael reaction of malonates to nitrooleolefins with chiral bifunctional organocatalysts, bearing both a thiourea and tertiary amino group, afforded Michael adducts with high yields and enantioselectivities.