Resolution of inherently chiral anti-O,O′-dialkylated calix[4]arenes and determination of their absolute stereochemistries by CD and X-ray methods

Fumitaka Narumi; Tetsutaro Hattori; Waka Yamabuki; Chizuko Kabuto; Hiroshi Kameyama

doi:10.1016/j.tetasy.2004.11.095

Resolution of inherently chiral anti-O,O′-dialkylated calix[4]arenes and determination of their absolute stereochemistries by CD and X-ray methods

Fumitaka Narumi, Tetsutaro Hattori, Waka Yamabuki, Chizuko Kabuto, Hiroshi Kameyama

ENG - Biomolecular Engineering

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

38 Citations (Scopus)

Abstract

Inherently chiral anti-O,O′-dibenzyl-p-tert-butylcalix[4]arene 1 was resolved as the (S)-2-methoxy-2-(naphthalen-1-yl)propionic ester by flash chromatography. Conversely, the anti-O,O′-dibutyl analogue 2 was resolved as the (S_a)-2′-methoxy-1,1′-binaphthalene-2-carboxylic ester by crystallization combined with flash chromatography. CD analysis of these compounds indicated the absolute stereochemistries to be (S _a)-(+)-1 and (S_a)-(+)-2, respectively, the former of which was confirmed by X-ray crystallographic analysis.

Original language	English
Pages (from-to)	793-800
Number of pages	8
Journal	Tetrahedron Asymmetry
Volume	16
Issue number	4
DOIs	https://doi.org/10.1016/j.tetasy.2004.11.095
Publication status	Published - 2005 Feb 21

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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Resolution of inherently chiral anti-O,O′-dialkylated calix[4]arenes and determination of their absolute stereochemistries by CD and X-ray methods. / Narumi, Fumitaka; Hattori, Tetsutaro; Yamabuki, Waka; Kabuto, Chizuko; Kameyama, Hiroshi.

In: Tetrahedron Asymmetry, Vol. 16, No. 4, 21.02.2005, p. 793-800.

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

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abstract = "Inherently chiral anti-O,O′-dibenzyl-p-tert-butylcalix[4]arene 1 was resolved as the (S)-2-methoxy-2-(naphthalen-1-yl)propionic ester by flash chromatography. Conversely, the anti-O,O′-dibutyl analogue 2 was resolved as the (Sa)-2′-methoxy-1,1′-binaphthalene-2-carboxylic ester by crystallization combined with flash chromatography. CD analysis of these compounds indicated the absolute stereochemistries to be (S a)-(+)-1 and (Sa)-(+)-2, respectively, the former of which was confirmed by X-ray crystallographic analysis.",

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AU - Kabuto, Chizuko

AU - Kameyama, Hiroshi

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