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Switched enantioselectivity by solvent components and temperature in photocyclodimerization of 2-anthracenecarboxylate with 6A,6X-diguanidio−γ-cyclodextrins

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Abstract A series of 6 A ,6 X -diguanidio- γ -cyclodextrins (CDs) were used as chiral hosts for mediating the enantiodifferentiating [4 + 4] photocyclodimerization of 2-anthracenecarboxylic acid (AC). These γ -CD… Click to show full abstract

Abstract A series of 6 A ,6 X -diguanidio- γ -cyclodextrins (CDs) were used as chiral hosts for mediating the enantiodifferentiating [4 + 4] photocyclodimerization of 2-anthracenecarboxylic acid (AC). These γ -CD derivatives form stable 1:2 ternary complexes with AC in aqueous ammonia solutions and the head-to-head photodimers 3 and 4 were greatly enhanced in the presence of these diguanidio- γ -CDs. The enantioselectivity of chiral photodimers 2 and 3 is a critical function of the temperature and the ammonia contents, showing inverted product chirality by changing these external factors.

Keywords: diguanidio cyclodextrins; photocyclodimerization; enantioselectivity solvent; switched enantioselectivity; solvent components; diguanidio

Journal Title: Chinese Chemical Letters
Year Published: 2018

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