Journal ArticleDOI
Organocatalysed asymmetric Mannich reactions.
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TLDR
This tutorial review provides an overview of the recent history of the asymmetric organocatalysed Mannich reaction, including scope and limitations, and application of different catalyst systems.Abstract:
The asymmetric Mannich reaction ranks among the most potent enantioselective and diastereoselective C–C-bond forming reactions. In recent years, organocatalysed versions of asymmetric Mannich processes have been increasingly reported and used in a rapidly growing number of applications. This tutorial review provides an overview of the recent history of the asymmetric organocatalysed Mannich reaction, including scope and limitations, and application of different catalyst systems.read more
Citations
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Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates
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Catalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update
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Asymmetric Organocatalytic Cyclization and Cycloaddition Reactions
Albert Moyano,Ramon Rios +1 more
Journal ArticleDOI
Recent Developments in Asymmetric Organocatalytic Domino Reactions
TL;DR: The field of asymmetric organocatalytic biomolecular cascades has become one of the most fascinating and current fields in organic chemistry as discussed by the authors, and the literature has been rapidly developing.
References
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Journal ArticleDOI
Mild and efficient deprotection of the amine protecting p-methoxyphenyl (PMP) group
Jorge M. M. Verkade,Lieke J. C. van Hemert,Peter J. L. M. Quaedflieg,Paul L. Alsters,Floris L. van Delft,Floris P. J. T. Rutjes +5 more
TL;DR: In this paper, mild and efficient procedures for deprotection of the amine nitrogen protecting p-methoxyphenyl (PMP) group are described, using trichloroisocyanuric acid (TCCA) and periodic acid.
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Chiral lithium(I) binaphtholate salts for the enantioselective direct Mannich-type reaction with a change of syn/anti and absolute stereochemistry.
TL;DR: Anti products were selectively obtained from acyclic ketoesters without epimerization at an alpha-tertiary-carbon center, and these are valuable since previous catalysts often gave syn/anti mixtures or the stereochemistry has not yet been determined.
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Development of the First Brønsted Acid Assisted Enantioselective Brønsted Acid Catalyzed Direct Mannich Reaction
TL;DR: The development of the first enantioselectiveBronsted acid assisted chiral Bronsted acid catalyzed direct Mannich reaction of acetophenone with various aldimines with good enantiOSElectivities and without the necessity of enolate preformation is described.
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A general organic catalyst for asymmetric addition of stabilized nucleophiles to acyl imines
TL;DR: In this article, Cinchona alkaloid-derived thiourea catalysts promote nucleophilic additions to acyl imines for the asymmetric synthesis of secondary amine adducts.
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Highly Diastereoselective Asymmetric Mannich Reactions of 1,3-Dicarbonyls with Acyl Imines
TL;DR: The cinchona alkaloids catalyze direct asymmetric Mannich reactions of cyclic 1,3-dicarbonyl compounds with acyl imines to afford alpha-quaternary carbon-bearing reaction products in yields of up to 98%, a diastereomeric excess of 90% or greater, and enantioselectivities up to 99% ee.