pH-Controlled Supramolecular Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate with Capped ?-Cyclodextrins
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 6A,6E-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.
2008 ◽
Vol 21
(6)
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pp. 395-404
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2016 ◽
Vol 4
(26)
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pp. 6287-6294
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2015 ◽
Vol 7
(44)
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pp. 24649-24655
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1971 ◽
Vol 32
(C5)
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pp. C5a-255-C5a-258