Stereodivergent Anion Binding Catalysis with Molecular Motors

Ruth Dorel, Ben L. Feringa*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

16 Citations (Scopus)
82 Downloads (Pure)

Abstract

A photoresponsive chiral catalyst based on an oligotriazole-functionalized unidirectional molecular motor has been developed for stereodivergent anion binding catalysis. The motor function controls the helical chirality of supramolecular assemblies with chloride anions, which by means of chirality transfer enables the enantioselective addition of a silyl ketene acetal nucleophile to oxocarbenium cations. Reversal of stereoselectivity (up to 142 % Δee) was achieved through rotation of the motor core induced by photochemical and thermal isomerization steps.

Original languageEnglish
Pages (from-to)785-789
Number of pages5
JournalAngewandte Chemie-International Edition
Volume59
Issue number2
DOIs
Publication statusPublished - 7-Jan-2020

Keywords

  • anion binding catalysis
  • molecular motors
  • oligotriazoles
  • photoswitches
  • stereodivergent catalysis
  • DYNAMIC CONTROL
  • NUCLEOPHILIC DEAROMATIZATION
  • REDOX CONTROL
  • LIGHT
  • ORGANOCATALYSIS
  • SWITCH

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