Direct and indirect single electron transfer (SET)-photochemical approaches for the preparation of novel phthalimide and naphthalimide-based lariat-type crown ethers
書誌事項
- 公開日
- 2014-02-27
- 権利情報
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- http://creativecommons.org/licenses/by/2.0
- http://creativecommons.org/licenses/by/2.0
- http://creativecommons.org/licenses/by/2.0
- DOI
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- 10.3762/bjoc.10.47
- 公開者
- Beilstein Institut
説明
<jats:p>In this review, we describe direct and indirect photochemical approaches that have been developed for the preparation of phthalimide- and naphthalimide-based, lariat-type crown ethers. The direct route utilizes a strategy in which nitrogen-linked side chains containing polyethoxy-tethered phthalimides and naphthalimides, possessing terminal α-trialkylsilyl groups, are synthesized utilizing concise routes and UV-irradiation to form macrocyclic ring systems. In contrast, the indirect route developed for the synthesis of lariat-type crown ethers employs sequences in which SET-promoted macrocyclization reactions of α-trialkylsilyl-terminated, polyethoxy-tethered phthalimides and naphthalimides are followed by a side chain introduction through substitution reactions at the amidol centers in the macrocyclic ethers. The combined observations made in these investigations demonstrate the unique features of SET-promoted photocyclization reactions that make them well-suited for the use in the synthesis of functionalized crown ethers. In addition, while some limitations exist for the general use of SET-photochemical reactions in large-scale organic synthesis, important characteristics of the photoinduced macrocyclization reactions make them applicable to unique situations in which high temporal and spatial control is required.</jats:p>
収録刊行物
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- Beilstein Journal of Organic Chemistry
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Beilstein Journal of Organic Chemistry 10 514-527, 2014-02-27
Beilstein Institut