Trifluoromethanesulfonic Acid, an Unusually Powerful Catalyst for the Michael Addition Reaction of β-Ketoesters under Solvent-Free Conditions

1999 ◽  
Vol 64 (10) ◽  
pp. 3770-3773 ◽  
Author(s):  
Hiyoshizo Kotsuki ◽  
Koji Arimura ◽  
Takeshi Ohishi ◽  
Ryosuke Maruzasa
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Trifluoromethanesulfonic Acid ◽  
Solvent Free ◽  
Michael Addition Reaction ◽  
Solvent Free Conditions ◽  
The Michael Addition

Use of (R)-Mandelic Acid as Chiral Co-Catalyst in the Michael Addition Reaction Organocatalyzed by (1S,4S)-2-Tosyl-2,5-diazabicyclo[2.2.1]heptane under Solvent-Free Conditions

2015 ◽  
Vol 2 (1) ◽  
Author(s):  
C. Gabriela Ávila-Ortiz ◽  
Manuel López-Ortiz ◽  
Alberto Vega-Peñaloza ◽  
Ignacio Regla ◽  
Eusebio Juaristi
Keyword(s):  
Michael Addition ◽  
Mandelic Acid ◽  
Addition Reaction ◽  
Solvent Free ◽  
Reaction Intermediates ◽  
Michael Addition Reaction ◽  
Co Catalyst ◽  
Co Catalysts ◽  
Solvent Free Conditions ◽  
The Michael Addition

AbstractThis article describes a study on the Michael addition reaction of cyclohexanone to nitroolefins catalyzed by the chiral secondary amine (1S,4S)-2-tosyl- 2,5-diazabicyclo[2.2.1]heptane. Reactions were carried out under solvent-free conditions to make them more environmentally friendly. Initially, the observed diastereoand enantioselectivities were moderate to good, but were significantly improved by lowering the reaction temperature. Furthermore, a variety of chiral acids were also tested as co-catalysts in both of their enantiomeric forms, which revealed that (R)-mandelic acid affords excellent results in terms of yield and stereoselectivity. Monitoring the reaction by MS-TOF allowed for the detection of key reaction intermediates, and a reasonable reaction mechanism in which both catalysts are involved is proposed.

A facile synthesis of β-amino carbonyl compounds through an aza-Michael addition reaction under solvent-free conditions

RSC Advances ◽  
2014 ◽  
Vol 4 (20) ◽  
pp. 10188 ◽  
Author(s):  
Chao Huang ◽  
Yanqing Yin ◽  
Jiahui Guo ◽  
Jiong Wang ◽  
Baomin Fan ◽  
...  
Keyword(s):  
Michael Addition ◽  
Carbonyl Compounds ◽  
Addition Reaction ◽  
Solvent Free ◽  
Michael Addition Reaction ◽  
Facile Synthesis ◽  
Solvent Free Conditions

Environmental Friendly Synthesis of Novel Isatin Ketal and Isatin Schiff Base Derivatives Using Michael Addition Reaction under Solvent-Free Conditions

2012 ◽  
Vol 30 (4) ◽  
pp. 891-899 ◽  
Author(s):  
Gholamhassan Imanzadeh ◽  
Zahra Soltanizadeh ◽  
Ali Khodayari ◽  
Mohammadreza Zamanloo ◽  
Yagoub Mansoori ◽  
...  
Keyword(s):  
Schiff Base ◽  
Michael Addition ◽  
Addition Reaction ◽  
Solvent Free ◽  
Michael Addition Reaction ◽  
Schiff Base Derivatives ◽  
Environmental Friendly ◽  
Solvent Free Conditions

Silicon-based thiourea-mediated and microwave-assisted thio-Michael addition under solvent-free reaction conditions

2011 ◽  
Vol 65 (5) ◽  
Author(s):  
Kamalakannan Prabakaran ◽  
Machindra Gund ◽  
Tae Kim ◽  
Euh Jeong ◽  
Chae Oh ◽  
...  
Keyword(s):  
Michael Addition ◽  
Carbonyl Compounds ◽  
Addition Reaction ◽  
Solvent Free ◽  
Michael Addition Reaction ◽  
Reaction Conditions ◽  
Microwave Assisted ◽  
Solvent Free Conditions ◽  
Silicon Based ◽  
Solvent Free Reaction

AbstractSilicon-based thiourea (SiliaBond® Thiourea) (Si-THU), a heterogeneous catalyst, has been applied to the highly selective C-S bond formation via Michael addition of thiols to α,β-unsaturated carbonyl compounds under solvent-free conditions at 55–60°C. The thio-Michael addition products were obtained in an excellent yield under optimised conditions. This methodology involving a metal-free as well as a metal scavenger catalyst has been found to be an alternative method for the thio-Michael addition reaction.

KF/Al2O3as a Highly Efficient, Green, Heterogeneous, and Reusable Catalytic System for the Solvent-Free Synthesis of Carboacyclic Nucleosides via Michael Addition Reaction

2008 ◽  
Vol 39 (1) ◽  
pp. 139-157 ◽  
Author(s):  
Abdolkarim Zare ◽  
Alireza Hasaninejad ◽  
Mohammad Hassan Beyzavi ◽  
Ahmad Reza Moosavi Zare ◽  
Ali Khalafi-Nezhad ◽  
...  
Keyword(s):  
Catalytic System ◽  
Michael Addition ◽  
Addition Reaction ◽  
Solvent Free ◽  
Michael Addition Reaction ◽  
Highly Efficient ◽  
Solvent Free Synthesis

Efficient Synthesis of 3-Amino-1,5-benzodiazepine-2-one Derivatives

Synlett ◽  
2017 ◽  
Vol 28 (10) ◽  
pp. 1183-1186 ◽  
Author(s):  
Nobuhiro Obara ◽  
Takeshi Watanabe ◽  
Tomohiro Asakawa ◽  
Toshiyuki Kan ◽  
Takao Tanaka
Keyword(s):  
Michael Addition ◽  
Convenient Method ◽  
Addition Reaction ◽  
Efficient Synthesis ◽  
Michael Addition Reaction ◽  
One Pot ◽  
Simple Method ◽  
The Michael Addition

A convenient method for synthesizing 3-amino-1,5-benzodiazepine-2-one via the Michael addition reaction of o-phenylenediamine with dehydroalanine ester derivatives, followed by cyclization, was developed. This simple method was used to obtain a variety of N-substituted 3-amino-1,5-benzodiazepine-2-ones in one pot with good yields.

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