First synthesis, isolation and characterization of enantiomerically pure and inherently chiral resorc[4]arenes by lewis acid cyclization of a resorcinol monoalkyl ether

Michael Klaes, Ceno Agena, Markus Köhler, Maki Inoue, Takehiko Wada, Yoshihisa Inoue, Jochen Mattay

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29 Citations (Scopus)

Abstract

Cyclization of resorcinol monoalkyl ethers with aliphatic aldehydes leads to the corresponding racemic mixtures of C4symmetric rccc-resorc[4]arenes. Separation of these isomers was achieved by mono-O-functionalization of the rccc2,8,14,20-tetramethylresorc[4]arene (2) with (S)-(+)-10-camphorsulfonyl chloride leading to a diastereomeric mixture of (+)-5a and (-)-5b. After removal of the chiral auxiliary the inherently chiral pure enantiomers (+)-2 and (-)-2 were obtained. Further enantiomerically pure rccc-resorc[4]arenes were obtained by cyclization of (+)-3-[(2S)-2-methylbutoxy]phenol (6) followed by chromatographic separation. The resulting diastereomeric resorc[4]arenes (+)-7a and (-)-7b were examined by CD spectroscopy, showing a perfect mirror image in all solvents examined. This indicates that the resorcarene cavities of (+)-7a and (-)-7b are essentially enantiomers of each other.

Original languageEnglish
Pages (from-to)1404-1409
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number8
DOIs
Publication statusPublished - 2003 Apr

Keywords

  • Asymmetric synthesis
  • Chirality
  • Circular dichroism
  • Monofunctionalization
  • Resorc[4]arenes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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