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

Research output: Contribution to journalArticlepeer-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 (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.

Original languageEnglish
Pages (from-to)793-800
Number of pages8
JournalTetrahedron Asymmetry
Volume16
Issue number4
DOIs
Publication statusPublished - 2005 Feb 21

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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