Mannich reaction

Definition: A carbon-carbon coupling reaction where ammonia or an amine reacts with a non-enolisable aldehyde, often methanal, and an enolisable carbonyl compound to form a beta-amino carbonyl compound.

ID: RXNO:0000032

Synonyms:

More about the RSC Name Reaction Ontology (RXNO)

Articles referencing this term

A two-directional approach to the anatoxin alkaloids: second synthesis of homoanatoxin and efficient synthesis of anatoxin-a
Stephen J. Roe and Robert A. Stockman, Chem. Commun., 2008 , 3432
DOI: 10.1039/b804304c

Highly enantioselective organocatalytic formation of a quaternary carbon center via chiral Brønsted acid catalyzed self-coupling of enamides
Christine Baudequin, Alexandru Zamfir and Svetlana B. Tsogoeva, Chem. Commun., 2008 , 4637
DOI: 10.1039/b804477e

Binaphthol-derived phosphoric acid as a versatile catalyst for enantioselective carbon–carbon bond forming reactions
Masahiro Terada, Chem. Commun., 2008 , 4097
DOI: 10.1039/b807577h

Design of chiral bifunctional secondary amine catalysts for asymmetric enamine catalysis
Taichi Kano and Keiji Maruoka, Chem. Commun., 2008 , 5465
DOI: 10.1039/b809301f

Enantioselective organocatalytic conjugate addition of α-aminoketone to nitroolefins
Sébastien Belot, Sarah Sulzer-Mossé, Stefan Kehrli and Alexandre Alexakis, Chem. Commun., 2008 , 4694
DOI: 10.1039/b810789k

New chemical and biological applications of fluorous technologies
Wei Zhang and Chun Cai, Chem. Commun., 2008 , 5686
DOI: 10.1039/b812433g

Asymmetric catalytic aza-Morita–Baylis–Hillman reaction (aza-MBH): an interesting functional group-caused reversal of asymmetric induction
Min Shi, Ming-Juan Qi and Xu-Guang Liu, Chem. Commun., 2008 , 6025
DOI: 10.1039/b814500h

Conjugated imines and iminium salts as versatile acceptors of nucleophiles
Makoto Shimizu, Iwao Hachiya and Isao Mizota, Chem. Commun., 2009 , 874
DOI: 10.1039/b814930e

Asymmetric organocatalytic Michael addition of ketones to vinyl sulfone
Qiang Zhu, Lili Cheng and Yixin Lu, Chem. Commun., 2008 , 6315
DOI: 10.1039/b816307c

Manipulation of fluorescent and colorimetric changes of fluorescein derivatives and applications for sensing silver ions
K. M. K. Swamy, Ha Na Kim, Jung Huyn Soh, Youngmee Kim, Sung-Jin Kim and Juyoung Yoon, Chem. Commun., 2009 , 1234
DOI: 10.1039/b819538b

An efficient copper-catalyzed oxidative Mannich reaction between tertiary amines and methyl ketones
Youming Shen, Mo Li, Sizhuo Wang, Tianguang Zhan, Ze Tan and Can-Cheng Guo, Chem. Commun., 2009 , 953
DOI: 10.1039/b819657e

A self-assembled chiral capsule with polar interior
Bogumił Kuberski and Agnieszka Szumna, Chem. Commun., 2009 , 1959
DOI: 10.1039/b820990a

Asymmetric catalysis with chiral primary amine-based organocatalysts
Li-Wen Xu, Jie Luo and Yixin Lu, Chem. Commun., 2009 , 1807
DOI: 10.1039/b821070e

Polycyclic alkaloids via transannular Mannich reactions
Paulo Vital, Masood Hosseini, M. Sundaram Shanmugham, Charlotte H. Gotfredsen, Pernille Harris and David Tanner, Chem. Commun., 2009 , 1888
DOI: 10.1039/b822955d

Oxidative coupling of amines and ketones by combined vanadium- and organocatalysis
Abhishek Sud, Devarajulu Sureshkumar and Martin Klussmann, Chem. Commun., 2009 , 3169
DOI: 10.1039/b901282f

Diphenylprolinol silyl ether as a catalyst in an asymmetric, catalytic and direct α-benzoyloxylation of aldehydes
Hiroaki Gotoh and Yujiro Hayashi, Chem. Commun., 2009 , 3083
DOI: 10.1039/b902287b

α,α-Dicyanoalkenes: versatile vinylogous nucleophiles for organic synthesis
Hai-Lei Cui and Ying-Chun Chen, Chem. Commun., 2009 , 4479
DOI: 10.1039/b906201g

Recent extensions of the Morita–Baylis–Hillman reaction
Guang-Ning Ma, Jia-Jun Jiang, Min Shi and Yin Wei, Chem. Commun., 2009 , 5496
DOI: 10.1039/b909405a

β-Amidoaldehydes via oxazoline hydroformylation
David S. Laitar, John W. Kramer, Bryan T. Whiting, Emil B. Lobkovsky and Geoffrey W. Coates, Chem. Commun., 2009 , 5704
DOI: 10.1039/b913698c

Brønsted acid activation of α-diazo imide: a syn-selective glycolate Mannich reaction
Timothy L. Troyer, Hubert Muchalski and Jeffrey N. Johnston, Chem. Commun., 2009 , 6195
DOI: 10.1039/b913785h

An asymmetric organocatalytic approach towards allylic amines and β-keto amino compounds
Christian Borch Jacobsen, Lennart Lykke, David Monge, Martin Nielsen, Lars Krogager Ransborg and Karl Anker Jørgensen, Chem. Commun., 2009 , 6554
DOI: 10.1039/b915439f

Solvent-free microwave-assisted multi-component reaction for preparation of 2-amino-1-aryl-2-(cyclohex-1-enyl)ethanones as precursors of pseudoephedrine analogues
Li-Jian Ma and Tsutomu Inokuchi, Chem. Commun., 2010 , 46 , 7037
DOI: 10.1039/c0cc00859a

Development of 5-silylethynyl-1,3-dioxolan-4-one as a new prochiral template for asymmetric phase-transfer catalysis
Takuya Hashimoto, Kazuhiro Fukumoto, Naoyuki Abe, Kazuki Sakata and Keiji Maruoka, Chem. Commun., 2010 , 46 , 7593
DOI: 10.1039/c0cc02334e

Asymmetric Brønsted acid catalysis in aqueous solution
Magnus Rueping and Thomas Theissmann, Chem. Sci., 2010 , 1 , 473
DOI: 10.1039/c0sc00206b