Issue 16, 2006
From the journal:

Chemical Communications

The first supramolecular photosensitization of enantiodifferentiating bimolecular reaction: anti-Markovnikov photoaddition of methanol to 1,1-diphenylpropene sensitized by modified β-cyclodextrin†

Gaku Fukuhara,a   Tadashi Mori,a   Takehiko Wadaab  and  Yoshihisa Inoue*ac  

* Corresponding authors

a Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Japan
E-mail: inoue@chem.eng.osaka-u.ac.jp
Fax: 81 6 6879 7923
Tel: 81 6 6879 7921

b PRESTO, JST, 2-1 Yamada-oka, Japan

c Entropy Control Project, ICORP, JST, 4-6-3 Kamishinden, Japan

Abstract

Enantiodifferentiating polar photoaddition of methanol to 1,1-diphenylpropene included and sensitized by cyanonaphthalene-modified β-cyclodextrin was examined for the first time to give optically active anti-Markovnikov adduct with accompanying inversion of the chiral sense of the photoproduct by temperature, which is entropic in origin.

Graphical abstract: The first supramolecular photosensitization of enantiodifferentiating bimolecular reaction: anti-Markovnikov photoaddition of methanol to 1,1-diphenylpropene sensitized by modified β-cyclodextrin

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Article information

DOI
https://doi.org/10.1039/B601674J
Article type
Communication
Submitted
03 Feb 2006
Accepted
27 Feb 2006
First published
20 Mar 2006

Chem. Commun., 2006, 1712-1714

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The first supramolecular photosensitization of enantiodifferentiating bimolecular reaction: anti-Markovnikov photoaddition of methanol to 1,1-diphenylpropene sensitized by modified β-cyclodextrin

G. Fukuhara, T. Mori, T. Wada and Y. Inoue, Chem. Commun., 2006, 1712 DOI: 10.1039/B601674J

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