Highly Stereoselective Photocyclodimerization of α-Cyclodextrin-Appended Anthracene Mediated by γ-Cyclodextrin and Cucurbit[8]uril: A Dramatic Steric Effect Operating Outside the Binding Site
Journal of the American Chemical Society2008Vol. 130(27), pp. 8574–8575
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Cheng Yang, Tadashi Mori, Yumi Origane, Young Ho Ko, Narayanan Selvapalam, Kimoon Kim, Yoshihisa Inoue
Abstract
Photocyclodimerization of alpha-cyclodextrin (CD)-appended anthracene was studied in the presence of gamma-CD and cucurbit[8]uril (CB[8]) hosts to manipulate the stereodifferentiating photoreaction occurring inside the cavity by the bulky attachment located outside. The gamma-CD-mediated photodimerization afforded the head-to-tail photodimers in 98% combined yield, in particular, the syn-head-to-tail photodimer of 91% ee in 68% yield, which are much greater than 32% ee and 44% yield obtained with unmodified anthracene carboxylate. The use of CB[8] also led to a striking inversion of the head-to-tail/head-to-head selectivity, affording exclusively the head-to-head photodimers in 99% combined yield.
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