Nucleophilic attacks on low LUMO compounds. Part 5. Radical-anionic nature of the transition state in the Michael addition reaction

1988 ◽  
Vol 110 (22) ◽  
pp. 7489-7493 ◽  
Author(s):  
Zeev. Gross ◽  
Shmaryahu. Hoz
Keyword(s):  
Transition State ◽  
Michael Addition ◽  
Addition Reaction ◽  
Michael Addition Reaction ◽  
The Michael Addition

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.

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.

scholarly journals Synthesis of 3,3′-arylmethylidenebis-4-hydroxycoumarin derivatives catalysed by KF-montmorillonite

2007 ◽  
Vol 2007 (10) ◽  
pp. 561-562 ◽  
Author(s):  
Nan Wu ◽  
Xinnian Li ◽  
Xin Xu ◽  
Daqing Shi
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Aromatic Aldehydes ◽  
Michael Addition Reaction ◽  
The Michael Addition

3,3′-Arylmethylidenebis-4-hydroxycoumarins derivatives have been synthesised in good yields by the Michael addition reaction of aromatic aldehydes with 4-hydroxycoumarin in DMF catalysed by KF-montmorillonite.

ChemInform Abstract: Development of New DMAP-Related Organocatalysts for Use in the Michael Addition Reaction of β-Ketoesters in Water.

ChemInform ◽  
2009 ◽  
Vol 40 (42) ◽  
Author(s):  
Kyungmin Ko ◽  
Keiji Nakano ◽  
Shigeru Watanabe ◽  
Yoshiyasu Ichikawa ◽  
Hiyoshizo Kotsuki
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Michael Addition Reaction ◽  
The Michael Addition
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