Highly stereoselective photocyclodimerization of alpha-cyclodextrin-appended anthracene mediated by gamma-cyclodextrin and cucurbit[8]uril: A dramatic steric effect operating outside the binding site
SCIE
SCOPUS
- Title
- Highly stereoselective photocyclodimerization of alpha-cyclodextrin-appended anthracene mediated by gamma-cyclodextrin and cucurbit[8]uril: A dramatic steric effect operating outside the binding site
- Authors
- Yang, C; Mori, T; Origane, Y; Ko, YH; Selvapalam, N; Kim, K; Inoue, Y
- Date Issued
- 2008-07-09
- Publisher
- AMER CHEMICAL SOC
- 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.
- Keywords
- ENANTIODIFFERENTIATING PHOTOCYCLODIMERIZATION; DIELS-ALDER; 2-ANTHRACENECARBOXYLATE; CATALYSIS; DERIVATIVES; ROTAXANES
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/22662
- DOI
- 10.1021/JA8032923
- ISSN
- 0002-7863
- Article Type
- Article
- Citation
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 130, no. 27, page. 8574 - 8575, 2008-07-09
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