Adsorption-induced asymmetric transformation of planar-chiral pyridinophanes

Nobuhiro Kanomata, Jun Oikawa

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Abstract

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
Volume44
Issue number18
DOIs
Publication statusPublished - 2003 Apr 28
Externally publishedYes

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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