Abstract
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.
Highlights
IntroductionAs a pioneer in this field, started developing new carbohydrate-based crown ethers and tested these compounds as catalysts in enantioselective reactions
It was found that the protecting group of the sugar unit in crown ethers 24 has an impact on the enantioselectivity, other crown compounds derived from glucose were synthesized
It was found that the protecting group of the sugar unit in crown ethers 24 a an impact on the enantioselectivity, other crown compounds derived from g were synthesized
Summary
As a pioneer in this field, started developing new carbohydrate-based crown ethers and tested these compounds as catalysts in enantioselective reactions. A variety of chiral crown ethers containing one or two sugar units in annulation with the macrocyclic ring from various monosaccharides and sugar alcohols were synthesized in our laboratory. These compounds generated significant asymmetric induction when used as chiral phase transfer catalysts in different reactions. Application as catalysts or investigation of crown compounds 1–3 have not been reported to date.
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