Adsorption-induced asymmetric transformation of planar-chiral pyridinophanes |
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Authors: | Nobuhiro Kanomata Jun Oikawa |
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Affiliation: | Department of Industrial Chemistry, Meiji University, Tama-ku, Kawasaki 214-8571, Japan |
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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. |
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