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Regulation of Chiral Phosphoric Acid Catalyzed Asymmetric Reaction through Crown Ether Based Host–Guest Chemistry

Jiadong Tang, Can Chen, Tao Hong, Zibin Zhang, Chunsong Xie, Shijun Li

2022Organic Letters16 citationsDOI

Abstract

Supramolecular asymmetric catalysis has arisen from the in-depth intersection of supramolecular chemistry and asymmetric catalysis due to its unique advantages in building chiral catalyst libraries and regulating performance of catalysts. Herein, we combine crown ether based host-guest chemistry with chiral phosphoric acid mediated asymmetric catalysis to actualize the supramolecular regulation of catalytic asymmetric two-component tandem acetalization reactions. By comparison with the catalytic reaction without host-guest interaction, improvement of up to 72% in yield and increases of up to 13% in enantioselectivity were acquired after addition of the alkali metal guests, which demonstrated the great advantages of this supramolecular regulation strategy.

Topics & Concepts

ChemistrySupramolecular chemistryCatalysisCrown etherSupramolecular catalysisPhosphoric acidOrganocatalysisCombinatorial chemistryEnantioselective synthesisSynergistic catalysisOrganic chemistryMoleculeIonMetal-Organic Frameworks: Synthesis and ApplicationsSupramolecular Chemistry and ComplexesCovalent Organic Framework Applications
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