Asymmetric Synthesis of Second-Generation Light-Driven Molecular Motors

Thomas van Leeuwen, Wojciech Danowski, Edwin Otten, Sander J Wezenberg, Ben L Feringa

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Abstract

The enantiomeric homogeneity of light-driven molecular motors based on overcrowded alkenes is crucial in their application as either unidirectional rotors or as chiral multistate switches. It was challenging to obtain these compounds as single enantiomers via the established synthetic procedures due to loss of optical purity in the key step, i.e., the Barton-Kellogg olefination reaction. Searching for strategies to avoid racemization, a new class of light-driven molecular motors was designed, synthesized, and studied. The stereochemical integrity was fully preserved throughout the synthesis, and on the basis of photochemical and kinetic studies using UV/vis, CD, and (1)H NMR spectroscopy, it was established that they still function properly as unidirectional molecular motors.

Original languageEnglish
Pages (from-to)5027-5033
Number of pages7
JournalThe Journal of Organic Chemistry
Volume82
Issue number10
DOIs
Publication statusPublished - 2017

Keywords

  • TETRASUBSTITUTED HELICAL ALKENES
  • CARBOPALLADATION/C-H-ACTIVATION
  • OVERCROWDED ALKENES
  • MACHINES
  • SWITCHES
  • DENSITY

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