Stereocontrol of molecular jump-rope: Crystallization-induced asymmetric transformation of planar-chiral cyclophanes

Nobuhiro Kanomata, Yoshiharu Ochiai

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Stereocontrol of planar-type cyclophanes was achieved by crystallization-induced asymmetric transformation in a molten state. Simply heating a 1/1 mixture of the solid and the liquid diastereoisomers of the bridged nicotinamides (S,3′S)-1 and (R,3′S)-2 effected the disequilibriation via rope-skipping isomerization to the solid sides, giving (S,3′S)-1 with up to 99% de.

Original languageEnglish
Pages (from-to)1045-1048
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number6
DOIs
Publication statusPublished - 2001 Feb 5
Externally publishedYes

Keywords

  • Crystallization-induced asymmetric transformation
  • Cyclophanes
  • Planar chirality
  • Rope-skipping isomerization
  • Stereocontrol

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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