Synthesis and optical resolution of an anti-O,O′-dialkylated calix[4]arene

Fumitaka Narumi; Waka Yamabuki; Tetsutaro Hattori; Hiroshi Kameyama; Sotaro Miyano

doi:10.1246/cl.2003.320

Synthesis and optical resolution of an anti-O,O′-dialkylated calix[4]arene

Fumitaka Narumi, Waka Yamabuki, Tetsutaro Hattori, Hiroshi Kameyama, Sotaro Miyano

ENG - Biomolecular Engineering

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

Proximally O,O′-disiloxane-bridged calix[4]arene (1) was treated with benzyl bromide in the presence of Cs₂CO₃ to afford, after desilylation, anti-O,O′-dibenzylcalix[4]arene (4a) in 90% yield. Chromatographic separation of its diastereomeric (S)-2-methoxy-2-(1-naphthyl)propionic esters allowed the first optical resolution of this kind of dialkylated calix[4]arenes.

Original language	English
Pages (from-to)	320-321
Number of pages	2
Journal	Chemistry Letters
Volume	32
Issue number	4
DOIs	https://doi.org/10.1246/cl.2003.320
Publication status	Published - 2003 Apr 5

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abstract = "Proximally O,O′-disiloxane-bridged calix[4]arene (1) was treated with benzyl bromide in the presence of Cs2CO3 to afford, after desilylation, anti-O,O′-dibenzylcalix[4]arene (4a) in 90% yield. Chromatographic separation of its diastereomeric (S)-2-methoxy-2-(1-naphthyl)propionic esters allowed the first optical resolution of this kind of dialkylated calix[4]arenes.",

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AU - Yamabuki, Waka

AU - Hattori, Tetsutaro

AU - Kameyama, Hiroshi

AU - Miyano, Sotaro

PY - 2003/4/5

Y1 - 2003/4/5

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AB - Proximally O,O′-disiloxane-bridged calix[4]arene (1) was treated with benzyl bromide in the presence of Cs2CO3 to afford, after desilylation, anti-O,O′-dibenzylcalix[4]arene (4a) in 90% yield. Chromatographic separation of its diastereomeric (S)-2-methoxy-2-(1-naphthyl)propionic esters allowed the first optical resolution of this kind of dialkylated calix[4]arenes.

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JF - Chemistry Letters

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ER -

Synthesis and optical resolution of an anti-O,O′-dialkylated calix[4]arene

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