scholarly journals New Advances in the Synthetic Application of Enantiomeric 1-Phenylethylamine (α-PEA): Privileged Chiral Inducer and Auxiliary

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 4907
Author(s):  
Marzena Wosińska-Hrydczuk ◽  
Jacek Skarżewski
Keyword(s):  
Natural Products ◽  
Chiral Auxiliary ◽  
Asymmetric Reactions ◽  
Chiral Resolution ◽  
Chiral Ligands ◽  
Diastereoselective Synthesis ◽  
New Developments ◽  
Synthetic Reactions ◽  
Medicinal Substances ◽  
Synthetic Application

New developments in the synthesis, resolution, and synthetic applications of chiral 1-phenylethylamine (α-PEA) reported in the last decade have been reviewed. In particular, improvements in the synthesis of α-PEA and its derivatives and chiral resolution, as well as their applications in the resolution of other compounds, were discussed. α-PEA was used as a chiral auxiliary in the diastereoselective synthesis of medicinal substances and natural products. Chiral ligands with α-PEA moieties were applied in asymmetric reactions, and effective modular chiral organocatalysts were constructed with α-PEA fragments and used in important synthetic reactions.

ChemInform Abstract: New Developments in Diastereoselective Synthesis of Drugs Derived from Natural Products

ChemInform ◽  
1989 ◽  
Vol 20 (17) ◽  
Author(s):  
W. BARTMANN ◽  
G. BECK ◽  
R. GEIGER ◽  
R. HENNING ◽  
V. TEETZ ◽  
...  
Keyword(s):  
Natural Products ◽  
Diastereoselective Synthesis ◽  
New Developments

Strategies of In Situ Generated Magnesium Catalysis in Asymmetric Reactions

Synlett ◽  
2021 ◽  
Author(s):  
Dongxu Yang ◽  
Linqing Wang
Keyword(s):  
Asymmetric Synthesis ◽  
Alkaline Earth ◽  
Earth Metal ◽  
Asymmetric Reactions ◽  
Chiral Ligands ◽  
Alkaline Earth Metal ◽  
Enantioselective Reactions ◽  
Earth's Crust

AbstractMagnesium (Mg) is a cheap, non-toxic, and recyclable alkaline earth metal that constitutes about 2% weight in the Earth’s crust. The use of magnesium catalysts to forge chiral moieties in molecules is highly attractive. Based on our work in recent years, we describe the current progress in the development of in situ generated magnesium catalysts and their application in asymmetric synthesis. In this perspective, a critically concise classification of in situ generated magnesium catalytic modes, with relevant examples, is presented, and representative mechanisms of each category are discussed. Building on the established diverse strategies, one can foresee that more innovative and structurally creative magnesium catalysts that are generated in situ will be developed to overcome more formidable challenges of catalytic enantioselective reactions.1 Introduction2 Magnesium Catalysts Generated in Situ from Chiral Ligands Containing Dual Reactive Hydrogens3 Magnesium Catalysts Generated in Situ from Monoanionic Chiral Ligands4 Bimetallic and Polymetallic Magnesium Catalysts Assembled in Situ5 Summary and Outlook

scholarly journals N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

2019 ◽  
Vol 15 ◽  
pp. 1722-1757
Author(s):  
Iwona E Głowacka ◽  
Aleksandra Trocha ◽  
Andrzej E Wróblewski ◽  
Dorota G Piotrowska
Keyword(s):  
Amino Acids ◽  
Natural Products ◽  
Natural Compounds ◽  
Review Article ◽  
Chiral Auxiliary ◽  
Biologically Relevant ◽  
Alternative Approaches ◽  
Approved Drugs ◽  
Enantioselective Syntheses ◽  
New Procedures

Since Garner’s aldehyde has several drawbacks, first of all is prone to racemization, alternative three-carbon chirons would be of great value in enantioselective syntheses of natural compounds and/or drugs. This review article summarizes applications of N-(1-phenylethyl)aziridine-2-carboxylates, -carbaldehydes and -methanols in syntheses of approved drugs and potential medications as well as of natural products mostly alkaloids but also sphingoids and ceramides and their 1- and 3-deoxy analogues and several hydroxy amino acids and their precursors. Designed strategies provided new procedures to several drugs and alternative approaches to natural products and proved efficiency of a 2-substituted N-(1-phenylethyl)aziridine framework as chiron bearing a chiral auxiliary.

scholarly journals Creations of Chiral Ligands Having Acetal Structures and Its Applications to Pd-catalyzed Asymmetric Reactions

2007 ◽  
Vol 65 (12) ◽  
pp. 1191-1202 ◽  
Author(s):  
Hiroto Nakano ◽  
Yuko Okuyama ◽  
Kouichi Takahashi ◽  
Reiko Fujita ◽  
Chizuko Kabuto
Keyword(s):  
Asymmetric Reactions ◽  
Chiral Ligands

scholarly journals Halonium-Induced Polyene Cyclizations

Synthesis ◽  
2019 ◽  
Vol 51 (08) ◽  
pp. 1753-1769 ◽  
Author(s):  
Agathe D’Hollander ◽  
Laure Peilleron ◽  
Tatyana Grayfer ◽  
Kevin Cariou
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Asymmetric Reactions ◽  
Recent Developments ◽  
Halogenated Natural Products

This review covers the methods that chemists have developed to access halogenated polycyclic structures from polyenes, by emulating Nature’s enzymatic machineries. From pioneering studies to the most recent developments, the different strategies, whether based on the use of standard reagents or on the design of specific ones, will be presented. Finally, asymmetric reactions and applications for the total synthesis of natural products will be exposed.1 Introduction2 Pioneering Studies3 Use of Specific Reagents4 Use of N-Haloamides5 Asymmetric Reactions6 Total Synthesis of Halogenated Natural Products7 Conclusion and Perspectives

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