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Ion Pair Catalyst - Pentanidinium.

Yimin Qin1, Zhenqiang Zhang1, Xinyi Ye1

  • 1College of Pharmaceutical Science & Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou, 310014, Zhejiang Province, P.R. China.

Chemical Record (New York, N.Y.)
|February 10, 2023
PubMed
Summary
This summary is machine-generated.

We developed N-sp2 hybrid pentanidinium as a phase-transfer catalyst for enhanced enantioselectivity in various organic reactions. This catalyst offers low loading and high stereocontrol, overcoming challenges in sp2 hybrid systems.

Keywords:
Asymmetric synthesisGuanidineIon pair catalysisPentanidiniumPhase-transfer catalysis

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • Traditional sp3 hybrid quaternary ammonium salts present steric challenges for substrate approach.
  • sp2 hybrid ammonium salts offer dual-direction ion pairing, posing difficulties in controlling reaction stereoselectivity.
  • Utilizing non-covalent interactions like hydrogen bonds and interactions can direct electrophile approach for improved enantioselectivity.

Purpose of the Study:

  • To design and develop a novel N-sp2 hybrid phase-transfer catalyst, pentanidinium.
  • To investigate the catalytic efficiency and enantioselectivity of pentanidinium in various organic transformations.
  • To demonstrate the advantages of pentanidinium over traditional catalysts in terms of stereocontrol and catalytic load.

Main Methods:

  • Design of N-sp2 hybrid pentanidinium featuring five conjugated nitrogen atoms, with one positively charged nitrogen for ion pair catalysis.
  • Application of pentanidinium in catalyzing α-hydroxylation, Michael addition, alkylation, and desymmetrization reactions.
  • Exploration of pentanidinium's efficacy in enantioconvergent halogenophilic nucleophilic substitution reactions, including azidation and thioesterification, with modified side chains.

Main Results:

  • Pentanidinium effectively catalyzed α-hydroxylation of 3-substituted-2-oxindoles and Michael addition of 3-alkyloxindoles with vinyl sulfone.
  • The catalyst facilitated alkylation of sulfenate anions and dihydrocoumarins, and desymmetrization of pro-chiral sulfinate to enantioenriched sulfinate esters.
  • Enantioconvergent halogenophilic nucleophilic substitution reactions, such as azidation and thioesterification, were efficiently catalyzed by modified pentanidinium structures.

Conclusions:

  • N-sp2 hybrid pentanidinium serves as an efficient phase-transfer and ion pair catalyst.
  • Pentanidinium demonstrates significant advantages, including low catalytic load and high enantioselectivity, in various organic reactions.
  • The designed catalyst provides a promising strategy for achieving stereocontrol in challenging asymmetric transformations.