Carbohydrate-Based Azacrown Ethers in Asymmetric Syntheses

Carbohydrate-based crown ethers represent a special group of chiral phase transfer catalysts. Several derivatives of these macrocycles have been synthesized in our research group. Among these compounds, monoaza-15-crown-5 lariat ethers proved to be effective phase transfer and enantioselective catal...

Full description

Saved in:
Bibliographic Details
Published inChemistry an international journal Vol. 3; no. 2; pp. 550 - 577
Main Authors Orbán, István, Bakó, Péter, Rapi, Zsolt
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.06.2021
Subjects
asymmetric synthesis
Asymmetry
Carbohydrates
Catalysis
Catalytic activity
crown ether
Crown ethers
Enantiomers
enantioselectivity
Epoxidation
Glucose
Nitrogen
Phase transfer catalysts
Online AccessGet full text

Cover

More Information
Summary:Carbohydrate-based crown ethers represent a special group of chiral phase transfer catalysts. Several derivatives of these macrocycles have been synthesized in our research group. Among these compounds, monoaza-15-crown-5 lariat ethers proved to be effective phase transfer and enantioselective catalysts in certain reactions. Those chiral azacrown ethers incorporating various carbohydrate moieties in the macrocyclic structure are reviewed, which generated asymmetric induction in reactions, such as Michael addition, epoxidation of enones, Darzens condensation and Michael-initiated ring-closure (MIRC) reaction. Effects on the catalytic activity of the structural changes are the focus.
ISSN:2624-8549
2624-8549
DOI:10.3390/chemistry3020039