Phase-transfer catalyzed asymmetric synthesis of α,β-unsaturated γ,γ-disubstituted γ-lactams

2017 ◽  
Vol 53 (35) ◽  
pp. 4779-4782 ◽  
Author(s):  
Alexander Arlt ◽  
Hideaki Toyama ◽  
Koji Takada ◽  
Takuya Hashimoto ◽  
Keiji Maruoka
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Chiral Phase

The direct, γ-selective vinylogous Michael addition of unsaturated γ-monosubstituted γ-lactams was realized by using chiral phase-transfer catalysis.

scholarly journals Asymmetric tandem hemiaminal-heterocyclization-aza-Mannich reaction of 2-formylbenzonitriles and amines using chiral phase transfer catalysis: an experimental and theoretical study

RSC Advances ◽  
2016 ◽  
Vol 6 (38) ◽  
pp. 31861-31870 ◽  
Author(s):  
Amedeo Capobianco ◽  
Antonia Di Mola ◽  
Valentina Intintoli ◽  
Antonio Massa ◽  
Vito Capaccio ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Mannich Reaction ◽  
Phase Transfer Catalysis ◽  
Theoretical Study ◽  
Phase Transfer ◽  
Chiral Phase

The first asymmetric synthesis of 3-amino-substituted isoindolinones was accomplished via cascade hemiaminal-heterocyclization-intramolecular aza-Mannich reaction of amines and 2-formylbenzonitriles using chiral phase transfer conditions (PTC).

scholarly journals Chiral Phase Transfer Catalysis in the Asymmetric Synthesis of a 3,3-Disubstituted Isoindolinone and Determination of Its Absolute Configuration by VCD Spectroscopy

Molecules ◽  
2020 ◽  
Vol 25 (10) ◽  
pp. 2272
Author(s):  
Guglielmo Monaco ◽  
Maximilian Tiffner ◽  
Antonia Di Mola ◽  
Wouter Herrebout ◽  
Mario Waser ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Absolute Configuration ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Vibrational Circular Dichroism ◽  
Target Compound ◽  
Chiral Phase ◽  
Catalytic Systems ◽  
High Yields

In this work we report our endeavors toward the development of an asymmetric synthesis of a 3,3-disubstituted isoindolinone, dimethyl 2-(1-methyl-3-oxoisoindolin-1-yl)malonate, via asymmetric cascade reaction of 2-acetylbenzonitrile with dimethylmalonate and the determination of its absolute configuration (AC) by vibrational circular dichroism (VCD). Bifunctional ammonium salts, derived from trans-1,2-cyclohexanediamine in combination with inorganic bases under phase transfer conditions, were the most effective catalytic systems, leading to the target in high yields and moderate enantioselectivity. An efficient process of heterochiral crystallization allowed the increase of the enantiopurity up to 96% ee and in an acceptable overall yield. An important aim of the present work is the comparison of different VCD methodologies for AC determination of the target compound.

ChemInform Abstract: Chiral Salen-Metal Complexes as Novel Catalysts for the Asymmetric Synthesis of α-Amino Acids under Phase Transfer Catalysis Conditions.

ChemInform ◽  
2010 ◽  
Vol 32 (30) ◽  
pp. no-no
Author(s):  
Yuri N. Belokon ◽  
Michael North ◽  
Tatiana D. Churkina ◽  
Nikolai S. Ikonnikov ◽  
Victor I. Maleev
Keyword(s):  
Amino Acids ◽  
Metal Complexes ◽  
Asymmetric Synthesis ◽  
Phase Transfer Catalysis ◽  
Phase Transfer

ChemInform Abstract: Enantioselective Photooxygenation of β-Keto Esters by Chiral Phase-Transfer Catalysis Using Molecular Oxygen.

ChemInform ◽  
2013 ◽  
Vol 44 (9) ◽  
pp. no-no
Author(s):  
Mingming Lian ◽  
Zhi Li ◽  
Yuanchun Cai ◽  
Qingwei Meng ◽  
Zhanxian Gao
Keyword(s):  
Molecular Oxygen ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Chiral Phase ◽  
Keto Esters

Michael Addition of 2-Phenylcyclohexanone to Chalcone Under Phase-Transfer Catalysis Conditions

1997 ◽  
pp. 181-189 ◽  
Author(s):  
Enrique Diez-Barra ◽  
Antonio de la Hoz ◽  
Sonia Merino ◽  
Prado Sánchez-Verdú
Keyword(s):  
Michael Addition ◽  
Phase Transfer Catalysis ◽  
Phase Transfer
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