pH-Controlled Supramolecular Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate with Capped γ-Cyclodextrins

Cheng Yang; Chenfeng Ke; Fujita Kahee; De-Qi Yuan; Tadashi Mori; Yoshihisa Inoue

doi:10.1071/CH08143

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pH-Controlled Supramolecular Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate with Capped γ-Cyclodextrins

Cheng Yang ^A , Chenfeng Ke ^A , Fujita Kahee ^B , De-Qi Yuan ^B ^C , Tadashi Mori ^A and Yoshihisa Inoue ^A ^C

+ Author Affiliations

- Author Affiliations

^A Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan.

^B Department of Molecular Medicinal Sciences, Nagasaki University, Bunkyo-machi 1-14, Nagasaki 852-8521, Japan.

^C Corresponding author. Email: inoue@chem.eng.osaka-u.ac.jp

Australian Journal of Chemistry 61(8) 565-568 https://doi.org/10.1071/CH08143
Submitted: 14 April 2008 Accepted: 15 May 2008 Published: 15 August 2008

Abstract

γ-Cyclodextrins capped with p-cresolbisbenzimidazole at the primary rim were synthesized and used as chiral hosts for mediating the enantiodifferentiating [4 + 4] photocyclodimerization of 2-anthracenecarboxylate. The use of 6^A,6^E-capped γ-cyclodextrin led to the formation of the anti-head-to-head photodimer in –5% enantiomeric excesses (ee) at pH 11 but in 28% ee at pH 6 with accompanying switching of product chirality, for which a pH-responsive conformational change of the capping moiety is likely to be responsible.

References

pH-Controlled Supramolecular Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate with Capped γ-Cyclodextrins

Abstract

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