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
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Journal ArticleDOI
A Combination of Visible-Light Organophotoredox Catalysis and Asymmetric Organocatalysis for the Enantioselective Mannich Reaction of Dihydroquinoxalinones with Ketones.
TL;DR: This protocol features very mild reaction conditions using simple and cheap catalysts for the synthesis of chiral quinoxaline derivatives with good to high yields and excellent enantioselectivities.
Journal ArticleDOI
Development of P-Spiro Chiral Aminophosphonium Salts as a New Class of Versatile Organic Molecular Catalyst
Daisuke Uraguchi,Takashi Ooi +1 more
TL;DR: A series of P-spiro chiral tetraaminophosphonium salts have been designed and synthesized as a new class of organic molecular catalysts, and their inherent abilities to exert four different, synthetically relevant asymmetric catalyses have been brought out through the unique molecular design on a single core structure, N4P+ as mentioned in this paper.
Journal ArticleDOI
α-Halo Amides as Competent Latent Enolates: Direct Catalytic Asymmetric Mannich-Type Reaction
TL;DR: Functional group interconversion of the 7-azaindoline amide moiety of the Mannich-adducts and further elaboration into a diamide without dehalogenation highlight the synthetic utility of the present protocol for accessing enantioenriched halogenated chemical entities.
Journal ArticleDOI
Simple and inexpensive threonine-based organocatalysts for the highly diastereo- and enantioselective direct large-scale syn-aldol and anti-Mannich reactions of α-hydroxyacetone
Chuanlong Wu,Xiangkai Fu,Shi Li +2 more
TL;DR: In this article, simple and inexpensive threonine-based organocatalysts that promote syn-aldol reactions and three-component asymmetric anti-Mannich reactions of α-hydroxyacetone achieving a respectable level of enantioselectivities are reported.
Journal ArticleDOI
List-Barbas-Mannich reaction catalyzed by modularly designed organocatalysts.
TL;DR: The List-Barbas-Mannich reaction of ethyl (p-methoxyphenylimino)acetate with unmodified aldehydes or ketones catalyzed by modularly designed organocatalysts that are self-assembled from proline and cinchona alkaloid thioureas produces the corresponding γ-oxo-α-amino acid derivatives in high yields and excellent stereoselectivities.
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.