Emergence of single-molecular chirality from achiral reactants

René R. E. Steendam, Jorge M.M. Verkade, Tim J.B. van Benthem, Hugo Meekes, Willem J.P. van Enckevort, Jan Raap, Floris P.J.T. Rutjes, Elias Vlieg

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Abstract

The synthesis of enantiopure molecules from achiral precursors without the need for pre-existing chirality is a major challenge associated with the origin of life. We here show that an enantiopure product can be obtained from achiral starting materials in a single organic reaction. An essential characteristic of this reaction is that the chiral product precipitates from the solution, introducing a crystal-solution interface which functions as an asymmetric autocatalytic system that provides sufficient chiral amplification to reach an enantiopure end state. This approach not only provides more insight into the origin of life but also offers a pathway to acquire enantiopure compounds for industrial applications.

Original languageEnglish
Article number5543
Number of pages8
JournalNature Communications
Volume5
DOIs
Publication statusPublished - 21 Nov 2014

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Keywords

  • aniline compounds
  • catalysis
  • crystallization
  • ketones
  • liquid crystals
  • molecular conformation
  • molecular structure
  • stereoisomerism

Cite this

Steendam, R. R. E., Verkade, J. M. M., van Benthem, T. J. B., Meekes, H., van Enckevort, W. J. P., Raap, J., ... Vlieg, E. (2014). Emergence of single-molecular chirality from achiral reactants. Nature Communications, 5, [5543]. https://doi.org/10.1038/ncomms6543