Stereospecific syntheses of macrobicyclic polyethers with carbon bridgeheads from chiral glycerol derivatives

Billy L. Allwood, Steven E. Fuller, Peter C Y K Ning, Alexandra M Z Slawin, J. Fraser Stoddart, David J. Williams

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

The [3.3.3]cryptand (3), prepared stereospecifically from 2,3-O-isopropylidene-D-glycerol d-(1) and 2,3-di-O-benzyl-L- glycerol L-(2), has been separated chromatographically at −5°C into slowly interconverting in-inii-(3) and out-out oo-(3) conformational diastereoisomers [ΔGii→oo = ca. 24 kcal moh−1 (1 kcal = 4.184 kJ) in CD3COCD3 at +38°C]; an X-ray structural analysis has shown (3) to form a crystalline 1:1 complex with Ba(SCN)2 in which the Ba2+ ion is encapsulated by oo-(3) and the two SCN− ions in an 11-co-ordinate manner.

Original languageEnglish (US)
Pages (from-to)1356-1360
Number of pages5
JournalJournal of the Chemical Society - Series Chemical Communications
Issue number20
DOIs
StatePublished - 1984

ASJC Scopus subject areas

  • Molecular Medicine

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