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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Journal ArticleDOI
Direct Catalytic Asymmetric Vinylogous Additions of α,β‐ and β,γ‐Butenolides to Polyfluorinated Alkynyl Ketimines
TL;DR: This is the first successful use of ketimines in the ProPhenol Mannich process, and the reaction offers a new approach for the preparation of pharmaceutically relevant products possessing trifluoromethylated tetrasubstituted alkylamines.
Journal ArticleDOI
Chiral γ‐Amino Amide Synthesis by Heterobimetallic Lanthanum/Lithium/Pybox‐Catalyzed Direct Asymmetric Mannich‐Type Reactions of α‐Keto Anilides
TL;DR: Direct catalytic asymmetric Mannich-type reactions of a-keto anilides 1 with various Nthiophenesulfonyl imines 2 are described, to enable the use of imines with various substituents in the synthesis of g-amino acid derivatives is in high demand.
Journal ArticleDOI
Proline-Mediated Enantioselective Construction of Tetrahydropyridines via a Cascade Mannich-Type/Intramolecular Cyclization Reaction
TL;DR: In this paper, a highly diastereo and enantioselective synthesis of 2,3-disubstituted tetrahydropyridines was accomplished via a proline-mediated cascade Mannich-type/intramolecular cyclization reaction from preformed N-PMP (p-methoxyphenyl) aldimines and inexpensive aqueous tetrahedro-2H-pyran-2,6-diol.
Journal ArticleDOI
Highly enantioselective three-component direct Mannich reactions of unfunctionalized ketones catalyzed by bifunctional organocatalysts.
Qunsheng Guo,John C.-G. Zhao +1 more
TL;DR: A highly stereoselective three-component direct Mannich reaction between aromatic aldehydes, p-toluenesulfonamide, and unfunctionalized ketones was achieved through an enolate mechanism for the first time with a bifunctional quinidine thiourea catalyst.
Journal ArticleDOI
2‐Pyrrolidinecarboxylic Acid Ionic Liquid as a Highly Efficient Organocatalyst for the Asymmetric One‐Pot Mannich Reaction
TL;DR: In this article, a one-pot three-component asymmetric Mannich reaction using [EMIm][Pro] as a catalyst has been developed, and a variety of optically active β-amino carbonyl compounds were synthesized in up to 99% yield with up to >99 dr and >99 ee.
References
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Book
Protective groups in organic synthesis
TL;DR: In this article, the most useful groups for the hydroxyl, amino, carboxyl, carbonyl, and sulfhydryl groups are discussed and the chemistry of the classes of these groups, as well as that of individual groups within the class using structures, equations and references.
Journal ArticleDOI
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.
Book
Greene's Protective Groups in Organic Synthesis
TL;DR: The role of protection groups in organic synthesis is discussed in this paper, where the authors present several general methods for phosphate Ester formation. But none of these methods are suitable for practical applications.
Journal ArticleDOI
Enantioselective Mannich‐Type Reaction Catalyzed by a Chiral Brønsted Acid
Journal ArticleDOI
Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation.
Daisuke Uraguchi,Masahiro Terada +1 more
TL;DR: It was found that the phosphoric acid derivatives of general structure 1 serve as highly effective catalysts for the direct addition of acetyl acetone to N-Boc-protected arylimines and functions as an excellent catalyst.