Adsorption-induced asymmetric transformation of planar-chiral pyridinophanes

Nobuhiro Kanomata; Jun Oikawa

doi:10.1016/S0040-4039(03)00699-3

Adsorption-induced asymmetric transformation of planar-chiral pyridinophanes

Nobuhiro Kanomata^*, Jun Oikawa

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

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 language	English
Pages (from-to)	3625-3628
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	18
DOIs	https://doi.org/10.1016/S0040-4039(03)00699-3
Publication status	Published - 2003 Apr 28
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(03)00699-3

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title = "Adsorption-induced asymmetric transformation of planar-chiral pyridinophanes",

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.",

author = "Nobuhiro Kanomata and Jun Oikawa",

note = "Funding Information: We thank Professor Takashi Tatsumi at Yokohama National University for his helpful suggestion and discussion. We also acknowledge PRESTO, Japan Science and Technology Corporation for financial support (1998-2002) and Catalysis Society of Japan for supply of reference catalysts.",

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T1 - Adsorption-induced asymmetric transformation of planar-chiral pyridinophanes

AU - Kanomata, Nobuhiro

AU - Oikawa, Jun

N1 - Funding Information: We thank Professor Takashi Tatsumi at Yokohama National University for his helpful suggestion and discussion. We also acknowledge PRESTO, Japan Science and Technology Corporation for financial support (1998-2002) and Catalysis Society of Japan for supply of reference catalysts.

PY - 2003/4/28

Y1 - 2003/4/28

N2 - 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.

AB - 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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U2 - 10.1016/S0040-4039(03)00699-3

DO - 10.1016/S0040-4039(03)00699-3

M3 - Article

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SN - 0040-4039

VL - 44

SP - 3625

EP - 3628

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

Adsorption-induced asymmetric transformation of planar-chiral pyridinophanes

Abstract

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