Supramolecular Photochirogenesis. 3. Enantiodifferentiating Photoisomerization of Cyclooctene Included and Sensitized by 6-O-Mono(o-methoxybenzoyl)–cyclodextrin

被引：0
作者：
Yunyan Gao
Maki inoue
Takehiko Wada
Yoshihisa Inoue
机构：
[1] The ICORP Entropy Control Project,Department of Molecular Chemistry
[2] Osaka University,undefined
来源：
Journal of inclusion phenomena and macrocyclic chemistry | 2004年 / 50卷
关键词：
asymmetric synthesis; cyclodextrin; cyclooctene; photochirogenesis; photoisomerization;
D O I：
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学科分类号：
摘要：
Supramolecular enantiodifferentiating photoisomerization of (Z)-cyclooctene (1Z) to chiral (E)-isomer (1E) through inclusion and sensitization by 6-O-mono(o-methoxybenzoyl)-β-cyclodextrin (2) was investigated in water and in aqueous methanol solutions at various temperatures. A dramatic inversion of the product chirality was observed to occur by simply changing the solvent from water to methanol. Thus, the supramolecular photosensitization in aqueous solution gave (R)-(–)-1E in 15% enantiomeric excess (ee), whereas in methanol the antipodal (S)-(+)-1E was obtained in 5% ee. The temperature and solvent dependencies of the product ee are discussed.
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页码：111 / 114
页数：3
相关论文
共 28 条
[1]  
Rau H(1983)␣ Chem Rev 83 535-undefined
[2]  
Inoue Y.(1992)undefined Chem Rev 92 741-undefined
[3]  
Feringa B.L.(1999)undefined Angew Chem Int Ed 38 3418-undefined
[4]  
van Delden R.A.(1996)undefined :J. Am. Chem. Soc. 118 1219-undefined
[5]  
Leibovitch M.(2002)undefined V. Tetrahedron Lett. 43 9335-undefined
[6]  
Olovsson G.(2003)undefined J. Am. Chem. Soc. 125 966-undefined
[7]  
Sundarababu G.(1982)undefined Acta Chim. Acad. Sci. Hung. 110 327-undefined
[8]  
Ramamurthy V.(2000)undefined J. Am. Chem. Soc. 122 406-undefined
[9]  
Scheffer J.R.(undefined)undefined undefined undefined undefined-undefined
[10]  
Trotter J.(undefined)undefined undefined undefined undefined-undefined
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