Journal ArticleDOI
Organocatalytic umpolung: N-heterocyclic carbenes and beyond
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TLDR
This tutorial review aims at offering a didactic overview of organocatalytic umpolung and should serve as an inspiration for further progress in this field.Abstract:
The umpolung strategy encompasses all the methods that make organic molecules react in an inverse manner compared to their innate polarity-driven reactivity. This concept entered the field of organocatalysis when it was recognized that N-heterocyclic carbenes (NHCs) can provide catalytic access to acyl anion equivalents. Since then, tremendous efforts have followed to develop a broad variety of NHC-catalyzed reactions. In addition to this, more recent research developments have shown that other families of organocatalysts are also able to mediate transformations in which inversion of polarity is involved. This tutorial review aims at offering a didactic overview of organocatalytic umpolung and should serve as an inspiration for further progress in this field.read more
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An overview of N-heterocyclic carbenes
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Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.
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References
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Journal ArticleDOI
N-heterocyclic carbenes: a new concept in organometallic catalysis.
TL;DR: N-Heterocyclic carbenes have become universal ligands in organometallic and inorganic coordination chemistry as mentioned in this paper, and they not only bind to any transition metal, be it in low or high oxidation states, but also to main group elements such as beryllium, sulfur, and iodine.
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Organocatalysis by N-Heterocyclic Carbenes
TL;DR: The inversion of the classical reactivity (Umpolung) opens up new synthetic pathways in biochemical processes as nucleophilic acylations and in nature, the coenzyme thiamine (vitamin B1), a natural thiazolium salt, utilizes a catalytic variant of this concept in biochemical process as nucleophile acylation.
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Asymmetric enamine catalysis.
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Proline-Catalyzed Direct Asymmetric Aldol Reactions
TL;DR: The finding that the amino acid proline is an effective asymmetric catalyst for the direct aldol reaction between unmodified acetone and a variety of aldehydes is reported.
Journal ArticleDOI
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.