2012年6月
High-Yield Diastereoselective Synthesis of Planar Chiral [2]- and [3]Rotaxanes Constructed from per-Ethylated Pillar[5]arene and Pyridinium Derivatives
CHEMISTRY-A EUROPEAN JOURNAL
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- 巻
- 18
- 号
- 24
- 開始ページ
- 7493
- 終了ページ
- 7500
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/chem.201200122
- 出版者・発行元
- WILEY-V C H VERLAG GMBH
Planar chiral [2]- and [3]rotaxanes constructed from pillar[5]arenes as wheels and pyridinium derivatives as axles were obtained in high yield using click reactions. The process of rotaxane formation was diastereoselective; the obtained [2]rotaxane was a racemic mixture consisting of (pS, pS, pS, pS, pS) and (pR, pR, pR, pR, pR) forms of the per-ethylated pillar[5]arene (C2) wheel, and other possible types of the [2]rotaxane did not form. Isolation of the enantiopure [2]rotaxanes with one axle through (pS, pS, pS, pS, pS)-C2 or (pR, pR, pR, pR, pR)-C2 wheels was accomplished. Furthermore, pillar[5]arene-based [3]rotaxane was successfully synthesized by attachment of two pseudo [2]rotaxanes onto a bifunctional linker. [3]Rotaxane formed in a 1:2:1 mixture with one axle threaded through two (pS, pS, pS, pS, pS)-C2, one (pS, pS, pS, pS, pS)-C2 and one (pR, pR, pR, pR, pR)-C2 (meso form), or two (pR, pR, pR, pR, pR)-C2 wheels. The [3]rotaxane enantiomers and the meso form were successfully isolated using appropriate chiral HPLC column chromatography. The procedure developed in this study is the starting point for the creation of pillar[5]arene-based interlocked molecules.
- リンク情報
- ID情報
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- DOI : 10.1002/chem.201200122
- ISSN : 0947-6539
- eISSN : 1521-3765
- ORCIDのPut Code : 25144635
- Web of Science ID : WOS:000304755700022