An aza-Michael addition protocol to fluoroalkylated β-amino acid derivatives and enantiopure trifluoromethylated N-heterocycles

2014 ◽  
Vol 16 (10) ◽  
pp. 4530-4534 ◽  
Author(s):  
Xing Yang ◽  
Zhuo Chen ◽  
Yuan Cai ◽  
Yi-Yong Huang ◽  
Norio Shibata
Keyword(s):  
Amino Acid ◽  
Michael Addition ◽  
Solvent Free ◽  
Amino Acid Derivatives ◽  
Solvent Free Conditions

Aza-Michael addition under catalyst- and solvent-free conditions worked well to install various fluoroalkylated amino acid derivatives and three trifluoromethylated heterocycles.

Highly Stereoselective Michael Addition Reactions of CamTHP*-Desymmetrized Glycinamide for the Synthesis of Functionally Dense Amino Acid Derivatives

2004 ◽  
Vol 6 (24) ◽  
pp. 4427-4429 ◽  
Author(s):  
Darren J. Dixon ◽  
Richard A. J. Horan ◽  
Nathaniel J. T. Monck ◽  
Paul Berg
Keyword(s):  
Amino Acid ◽  
Michael Addition ◽  
Amino Acid Derivatives ◽  
Addition Reactions

Highly efficient regioselective synthesis of pyrroles via a tandem enamine formation–Michael addition–cyclization sequence under catalyst- and solvent-free conditions

2015 ◽  
Vol 17 (6) ◽  
pp. 3415-3423 ◽  
Author(s):  
Thavaraj Vivekanand ◽  
Perumal Vinoth ◽  
B. Agieshkumar ◽  
Natarajan Sampath ◽  
Arumugam Sudalai ◽  
...  
Keyword(s):  
Column Chromatography ◽  
Michael Addition ◽  
Solvent Free ◽  
Regioselective Synthesis ◽  
Highly Efficient ◽  
Solvent Free Conditions ◽  
Enamine Formation

An efficient three-component, catalyst-, solvent-, and column chromatography-free procedure was developed for the synthesis of 3-(1H-pyrrol-3-yl)indolin-2-ones.

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.

Enantioselective conjugate addition of hydroxylamines to α,β-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal Rh(iii) complex

2017 ◽  
Vol 4 (4) ◽  
pp. 573-577 ◽  
Author(s):  
Tao Deng ◽  
Ganesh Kumar Thota ◽  
Yi Li ◽  
Qiang Kang
Keyword(s):  
Amino Acid ◽  
Michael Addition ◽  
Conjugate Addition ◽  
Amino Acid Derivatives ◽  
Highly Efficient

A highly efficient chiral-at-metal Rh(iii) complex catalyzed asymmetric aza-Michael addition was developed, affordingN-protected β-amino acid derivatives with excellent enantioselectivity.

scholarly journals Substrate-controlled Diastereoselective Michael Addition of Alkylidene Malonates by Grignard Reagents

2019 ◽  
Vol 25 (1) ◽  
pp. 116-121
Author(s):  
Wei Zhou ◽  
Qingwei Xiao ◽  
Yuanyuan Chang ◽  
Qifa Liu ◽  
Xiaohao Zang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Chiral Auxiliary ◽  
Grignard Reagents ◽  
Amino Acid Derivatives ◽  
Catalyst Free ◽  
Chemical Efficiency

AbstractHerein is described a diastereoselective Michael addition of Grignard reagents to α, β- unsaturated diethyl malonates incorporated with a 2-oxazolidone chiral auxiliary. The catalyst-free Michael addition proceeds with good chemical efficiency and excellent stereoselectivity; and it provides new thoughts to the asymmetric synthesis of β-substituted β3 amino acid derivatives.

scholarly journals Cyanuric Chloride-Catalyzed Michael Addition of Indoles to Nitroolefins under Solvent-Free Conditions

2013 ◽  
Vol 2013 ◽  
pp. 1-5
Author(s):  
Xiao Juan Yang ◽  
Yun Jing
Keyword(s):  
Michael Addition ◽  
Present Method ◽  
Solvent Free ◽  
Cyanuric Chloride ◽  
Reaction Conditions ◽  
Experimental Procedure ◽  
Solvent Free Conditions ◽  
Short Period ◽  
The Michael Addition ◽  
Solvent Free Reaction

Cyanuric chloride is an inexpensive, efficient, and mild catalyst for the Michael addition of indoles to nitroolefins at 70°C under solvent-free conditions. The simple experimental procedure, solvent-free reaction conditions, utilization of an inexpensive and readily available catalyst, short period of conversion, and excellent yields are the advantages of the present method.

scholarly journals Green Michael addition of thiols to electron deficient alkenes using KF/alumina and recyclable solvent or solvent-free conditions

2009 ◽  
Vol 20 (1) ◽  
pp. 93-99 ◽  
Author(s):  
Eder J. Lenardão ◽  
Danusia O. Trecha ◽  
Patrícia da C. Ferreira ◽  
Raquel G. Jacob ◽  
Gelson Perin
Keyword(s):  
Michael Addition ◽  
Solvent Free ◽  
Solvent Free Conditions
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