Journal ArticleDOI
Organocatalysed asymmetric Mannich reactions.
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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Multicomponent double Mannich alkylamination involving C(sp2)–H and benzylic C(sp3)–H bonds
Zhencheng Lai,Rongkai Wu,Jiaming Li,Xing Chen,Linwei Zeng,Xi Wang,Jingjing Guo,Zujin Zhao,Hironao Sajiki,Sunliang Cui +9 more
TL;DR: In this article , the double Mannich reaction was used for both C(sp2)-H and unactivated benzylic c(sp3)-H bonds, and an unprecedented multicomponent double-Mannich alkylamination was reported, where various 3-alkylbenzofurans, formaldehyde and alkylorine hydrochlorides assembled efficiently to furnish benzofuran-fused piperidines.
Journal ArticleDOI
Cu(I)-Catalyzed Asymmetric Mannich Reaction of Glycine Schiff Bases to Ketimines.
TL;DR: A copper-catalyzed asymmetric Mannich reaction between glycine Schiff bases and ketimines has been developed that afforded 2-oxindole-based chiral syn-α,β-diamino acid derivatives in high yields with good-to-excellent diastereoselectivities and excellent enantioselectivity.
Journal ArticleDOI
Enantioselective anti-Mannich reaction catalyzed by modularly designed organocatalysts.
Swapna Konda,John C.-G. Zhao +1 more
TL;DR: A highly stereoselective method for achieving the anti-Mannich reaction of aldehydes and ketones with ethyl (4-methoxyphenylimino)acetate was realized using the modularly designed organocatalysts self-assembled from cinchona alkaloid derivatives and (A)-pyrrolidien-3-carboxylic acid in the reaction media.
Journal ArticleDOI
Enantioselective synthesis of β-amino esters bearing a quinazoline moiety via a Mannich-type reaction catalyzed by a cinchona alkaloid derivative
TL;DR: The cinchona alkaloids catalyzed the direct asymmetric Mannich reactions of 1, 3-dicarbonyl compounds with acyl imines to produce novel β-amino ester derivatives containing a quinazoline moiety as discussed by the authors.
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.