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
Journal ArticleDOI
Catalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update
Journal ArticleDOI
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
The Scope of the Direct Proline-Catalyzed Asymmetric Addition of Ketones to Imines
Wolfgang Notz,Shin-ichi Watanabe,Naidu S. Chowdari,Guofu Zhong,Juan M. Betancort,Fujie Tanaka,Carlos F. Barbas +6 more
TL;DR: The methodology developed was applied as a powerful approach toward the synthesis of enantiomerically pure functionalized α-amino acids, γ-lactones, oxime-functionalized amino acids as well as pharmacologically important targets such as (R)-cyclohexylglycine.
Journal ArticleDOI
Expedient synthesis of chiral 1,2- and 1,4-diamines: protecting group dependent regioselectivity in direct organocatalytic asymmetric Mannich reactions.
TL;DR: An organocatalytic asymmetric Mannich reaction of protected amino ketones with imines in the presence of an L-proline-derived tetrazole catalyst afforded diamines with excellent yields and enantioselectivities of up to 99%.
Journal ArticleDOI
A Highly Active 4-Siloxyproline Catalyst for Asymmetric Synthesis
Yujiro Hayashi,Junichiro Yamaguchi,Kazuhiko Hibino,Tatsunobu Sumiya,Tatsuya Urushima,Mitsuru Shoji,Daisuke Hashizume,Hiroyuki Koshino +7 more
TL;DR: Trans-4-tert-Butyldimethylsiloxy-L-proline displays a greater catalytic activity than the parent proline without compromising the enantioselectivity, which widens the substrate scope in the α-aminoxylation of carbonyl compounds as mentioned in this paper.
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Chiral Brønsted acid-catalyzed enantioselective multicomponent Mannich reaction: synthesis of anti-1,3-diamines using enecarbamates as nucleophiles.
TL;DR: Reaction of aldehydes 2, anilines 3, and enecarbamates 4 in dichloromethane in the presence of EtOH and a catalytic amount of chiral phosphoric acid afforded the Mannich adducts which were in situ reduced to anti-1,2-disubstituted 1,3-diamines 1 in excellent diastereoselectivity and enantioselectivities.
Journal ArticleDOI
Direct catalytic asymmetric anti-selective Mannich-type reactions
Ismail Ibrahem,Armando Córdova +1 more
TL;DR: The simple chiral pyrrolidine catalyzed asymmetric anti-selective Mannich-type reaction is presented; the reaction gives the corresponding amino acid derivatives with 10:1- >19:1 dr and 97-99% ee.