A rapid and highly enantioselective C–11C bond formation of l-[11C]phenylalanine via chiral phase-transfer catalysis

2017 ◽  
Vol 15 (3) ◽  
pp. 570-575 ◽  
Author(s):  
Aleksandra Pekošak ◽  
Ulrike Filp ◽  
Janja Škrinjar ◽  
Alex J. Poot ◽  
Albert D. Windhorst
Keyword(s):  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Bond Formation ◽  
Chiral Phase

Multistep asymmetric phase-transfer catalyzed carbon-11 benzylation for the enantioselective radiolabeling of l- and d-[11C]phenylalanine.

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

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 Catalysts with Hydrogen Bond: A Powerful Tool in the Asymmetric Synthesis

Catalysts ◽  
2019 ◽  
Vol 9 (3) ◽  
pp. 244 ◽  
Author(s):  
Hongyu Wang
Keyword(s):  
Organic Synthesis ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Chiral Phase ◽  
Design Synthesis ◽  
Phase Transfer Catalysts ◽  
The Past ◽  
Hydrogen Bonding Interactions ◽  
Chiral Phase Transfer Catalysts ◽  
Made In

Asymmetric phase-transfer catalysis has been widely applied into organic synthesis for efficiently creating chiral functional molecules. In the past decades, chiral phase-transfer catalysts with proton donating groups are emerging as an extremely significant strategy in the design of novel catalysts, and a large number of enantioselective reactions have been developed. In particular, the proton donating groups including phenol, amide, and (thio)-urea exhibited unique properties for cooperating with the phase-transfer catalysts, and great advances on this field have been made in the past few years. This review summarizes the seminal works on the design, synthesis, and applications of chiral phase-transfer catalysts with strong hydrogen bonding interactions.

scholarly journals Review on Asymmetric Transformations with Chiral Phase-Transfer Catalysts

2019 ◽  
pp. 6-12
Author(s):  
Tesfaye Tebeka ◽  
Atitegebe Abera
Keyword(s):  
Unnatural Amino Acids ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Biological Activities ◽  
Industrial Applications ◽  
Cinchona Alkaloids ◽  
Chiral Phase ◽  
Asymmetric Transformations ◽  
Phase Transfer Catalysts ◽  
Chiral Phase Transfer Catalysts

This review focuses onasymmetric transformations with Chiral Phase-Transfer Catalysts and its application. Phase-transfer catalysis is practical methodology for organic synthesis. It is possible to achieve highly enantio selective transformations under phase-transfer conditions for a variety of ─C─C─ ─C─O─ and ─C─N─ bond-forming reactions. The asymmetric transformations using modified cinchona alkaloids, chiral spiro ammonium salts and crown ether are among the primary source of effective chiral phase-transfer catalyst, which allows access to enantiomerically pure unnatural amino acids and synthetically useful adducts containing quaternary stereogenic centers. The advantage of this method is its simple experimental procedure, large chiral pool, mild reaction condition, inexpensive, environmentally benign reagent and use of simple and inexpensive reactants. Nowadays, it appears to be the most important synthetic method used in various fields of organic chemistry, and also found widespread industrial applications. This review summarizes the synthesis application, enantio selective transformation of some selected reaction, biological activities and catalytic activities of Phase-transfer catalysis and especial emphasis is given for organo catalysis. In asymmetric organo catalyst, it is possible to obtain chiral organic products in high enantio enriched form by steric hindrance approach method. The advantage of organic molecules as chiral catalysts complements the traditional organo-metallic and biological approaches to asymmetric catalysis.

scholarly journals Vinylogous and Arylogous Stereoselective Base-Promoted Phase-Transfer Catalysis

Catalysts ◽  
2021 ◽  
Vol 11 (12) ◽  
pp. 1545
Author(s):  
Assunta D’Amato ◽  
Giorgio Della Sala
Keyword(s):  
Organic Synthesis ◽  
Phase Transfer Catalysis ◽  
Negative Charge ◽  
Phase Transfer ◽  
Bond Formation ◽  
Metal Catalysis ◽  
Carbon Nucleophiles ◽  
Unsaturated Compounds

Vinylogous enolate and enolate-type carbanions, generated by deprotonation of α,β-unsaturated compounds and characterized by delocalization of the negative charge over two or more carbon atoms, are extensively used in organic synthesis, enabling functionalization and C–C bond formation at remote positions. Similarly, reactions with electrophiles at benzylic and heterobenzylic position are performed through generation of arylogous and heteroarylogous enolate-type nucleophiles. Although widely exploited in metal-catalysis and organocatalysis, it is only in recent years that the vinylogy and arylogy principles have been translated fruitfully in phase-transfer catalyzed processes. This review provides an overview of the methods developed to date, involving vinylogous and (hetero)arylogous carbon nucleophiles under phase-transfer catalytic conditions, highlighting main mechanistic aspects.

scholarly journals Asymmetric trifluoromethylthiolation of azlactones under chiral phase transfer catalysis

2020 ◽  
Vol 18 (15) ◽  
pp. 2914-2920
Author(s):  
Marina Sicignano ◽  
Ricardo I. Rodríguez ◽  
Vito Capaccio ◽  
Fabio Borello ◽  
Rafael Cano ◽  
...  
Keyword(s):  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Present Communication ◽  
Chiral Phase

The first enantioselective method for the installation of the SCF3 group at the C-4 position of azlactones is described in the present communication under quinidinium phase transfer catalysis.

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