An efficient procedure for the synthesis and isolation of (+)-(2R,3R,11R,12R)- and (-)-(2S,3S,11S,12S)-tetraphenyl-18-crown-6

John Crosby*, Martin E. Fakley, Colin Gemmell, Keith Martin, Andrew Quick, Alexandra M Z Slawin, Hooshang Shahriari-Zavareh, J. Fraser Stoddart, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

The enantiomers of the chiral 2,3-diphenyl- and 2,3,11,12-tetraphenyl-1,4,7,10,13,16-hexaoxacyclooctadecanes have been prepared in single step reactions from the readily-available chiral precursors, (RR)- and (SS)-hydrobenzoins, followed by bulk isolations of the pure 18-crown-6 derivatives via their 1:1 crystalline complexes with potassium nitrate (for the diphenyl derivative) or calcium nitrate (for the tetraphenyl derivative), obtained directly from the worked-up crude reaction mixtures: X-ray crystal structures characterise the uncomplexed (RRRR)-tetraphenyl-18-crown-6 and the 1:1 complex formed between its (SSSS)-enantiomer and calcium nitrate.

Original languageEnglish (US)
Pages (from-to)3849-3852
Number of pages4
JournalTetrahedron Letters
Volume30
Issue number29
DOIs
StatePublished - 1989

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'An efficient procedure for the synthesis and isolation of (+)-(2R,3R,11R,12R)- and (-)-(2S,3S,11S,12S)-tetraphenyl-18-crown-6'. Together they form a unique fingerprint.

Cite this