Adsorption-induced asymmetric transformation of planar-chiral pyridinophanes

Nobuhiro Kanomata*, Jun Oikawa

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)


Stereocontrol of cyclophane-type planar chirality was investigated via adsorption-induced asymmetric transformation (AIAT) on a series of inorganic porous adsorbents. The rope-skipping equilibria between bridged nicotinamides (S,3′S)-1 and (R,3′S)-2 shifted preferentially to (R,3′S)-2 to accumulate (R)-configuration of planar chirality with up to 61% de (ca. 4/1 ratio) on alumina. The results are in good contrast to accumulation of the corresponding (S)-configuration via conventional crystallization-induced asymmetric transformation (CIAT) to the solid (S,3′S)-1a-d.

Original languageEnglish
Pages (from-to)3625-3628
Number of pages4
JournalTetrahedron Letters
Issue number18
Publication statusPublished - 2003 Apr 28
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


Dive into the research topics of 'Adsorption-induced asymmetric transformation of planar-chiral pyridinophanes'. Together they form a unique fingerprint.

Cite this