Self-replication and amplification of enantiomeric excess of chiral multifunctionalized large molecules by asymmetric autocatalysis

Tsuneomi Kawasaki, Mai Nakaoda, Yutaro Takahashi, Yusuke Kanto, Nanako Kuruhara, Kenji Hosoi, Itaru Sato, Arimasa Matsumoto, Kenso Soai

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

Self-replication of large chiral molecular architectures is one of the great challenges and interests in synthetic, systems, and prebiotic chemistry. Described herein is a new chemical system in which large chiral multifunctionalized molecules possess asymmetric autocatalytic self-replicating and self-improving abilities, that is, improvement of their enantioenrichment in addition to the diastereomeric ratio. The large chiral multifunctionalized molecules catalyze the production of themselves with the same structure, including the chirality of newly formed asymmetric carbon atoms, in the reaction of the corresponding achiral aldehydes and reagent. The chirality of the large multifunctionalized molecules controlled the enantioselectivity of the reaction in a highly selective manner to construct multiple asymmetric stereogenic centers in a single reaction.

Original languageEnglish
Pages (from-to)11199-11202
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number42
DOIs
Publication statusPublished - 2014 Oct 1

Keywords

  • Asymmetric amplification
  • Asymmetric catalysis
  • Autocatalysis
  • Chirality
  • Enantioselectivity

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

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