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...
| Veröffentlicht in: | Langmuir : the ACS journal of surfaces and colloids. - 1992. - 26(2010), 2 vom: 19. Jan., Seite 782-5 |
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| Weitere Verfasser: | , , , |
| Format: | Online-Aufsatz |
| Sprache: | English |
| Veröffentlicht: |
2010
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| Zugriff auf das übergeordnete Werk: | Langmuir : the ACS journal of surfaces and colloids |
| Schlagworte: | Journal Article |
| Zusammenfassung: | 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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| Beschreibung: | Date Completed 11.03.2010 Date Revised 13.01.2010 published: Print Citation Status PubMed-not-MEDLINE |
| ISSN: | 1520-5827 |
| DOI: | 10.1021/la902176e |