Stepwise photochemical-chiral delivery in gamma-cyclodextrin-directed enantioselective photocyclodimerization of methyl 3-methoxyl-2-naphthoate in aqueous solution

Irradiation of methyl 3-methoxyl-2-naphthoate (2,3-NA) with lambda > 280 nm results in photocyclodimerization to produce cubane-like photocyclodimer 1 and the [4 + 4] intermediate 2. The optically pure enantiomers of the intermediate 2 have been achieved by high-performance liquid chromatography...

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Veröffentlicht in:Langmuir : the ACS journal of surfaces and colloids. - 1992. - 26(2010), 2 vom: 19. Jan., Seite 782-5
1. Verfasser: Luo, Lin (VerfasserIn)
Weitere Verfasser: Cheng, Su-Fang, Chen, Bin, Tung, Chen-Ho, Wu, Li-Zhu
Format: Online-Aufsatz
Sprache:English
Veröffentlicht: 2010
Zugriff auf das übergeordnete Werk:Langmuir : the ACS journal of surfaces and colloids
Schlagworte:Journal Article
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245 1 0 |a Stepwise photochemical-chiral delivery in gamma-cyclodextrin-directed enantioselective photocyclodimerization of methyl 3-methoxyl-2-naphthoate in aqueous solution 
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520 |a Irradiation of methyl 3-methoxyl-2-naphthoate (2,3-NA) with lambda > 280 nm results in photocyclodimerization to produce cubane-like photocyclodimer 1 and the [4 + 4] intermediate 2. The optically pure enantiomers of the intermediate 2 have been achieved by high-performance liquid chromatography (HPLC) resolution on a chiralcel OJ-RH column. Comparison of the enantiomeric excess (ee) values for photocyclodimer 1 and the intermediate 2 obtained in gamma-CD aqueous solution reveals the stepwise photochemical-chiral delivery for the first time, which is recognized to be a consequence of an in situ increase in the ee value from 39% for the [4 + 4] intermediate 2 to 48% for photocyclodimer 1 upon irradiation of 2,3-NA in the presence of gamma-CD 
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700 1 |a Cheng, Su-Fang  |e verfasserin  |4 aut 
700 1 |a Chen, Bin  |e verfasserin  |4 aut 
700 1 |a Tung, Chen-Ho  |e verfasserin  |4 aut 
700 1 |a Wu, Li-Zhu  |e verfasserin  |4 aut 
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