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Recognition and activation by ureas and thioureas: stereoselective reactions using ureas and thioureas as hydrogen-bonding donors

Organic & Biomolecular Chemistry · 2005 · Vol. 3(24) · pp. 4299–4299
Yoshiji Takemoto

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.

Chemical Synthesis and AnalysisAsymmetric Synthesis and CatalysisFluorine in Organic ChemistryChemistryThioureaCatalysisHydrogen bondUreaEnantioselective synthesisCombinatorial chemistryStereoselectivityHydrogenHydrogen bond catalysis

MeSH terms

CatalysisCyclizationHydrogen BondingStereoisomerismSulfhydryl CompoundsUrea
Citations
765
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13.49
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References
H-Bonding Additives Act Like Lewis Acid Catalysts
Organic Letters · 2002 · 462 citations
Encoding and decoding hydrogen-bond patterns of organic compounds
Accounts of Chemical Research · 1990 · 4,564 citations
In the Golden Age of Organocatalysis
Angewandte Chemie International Edition · 2004 · 2,568 citations
Asymmetric organocatalysis
Organic & Biomolecular Chemistry · 2005 · 1,116 citations
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