The supramolecular structures and reactivities of some complexes of chiral crown ethers with borane ammonia

Hooshang Shahriari-Zavareh*, J. Fraser Stoddart, M. Kevin Williams, Billy L. Allwood, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

Whereas 1 : 1 crystalline complexes have been isolated between borane ammonia and methyl 4,6-O-benzylidene-2,3-dideoxy-α-d-galactopyranosido [2,3-b]-1,4,7,10,13,16-hexaoxacyclo-octadecane (1), methyl 4,6-O-benzylidene-2,3-dideoxy-α-d-mannopyranosido [2,3-b] (methyl 4′,6′-O-benzylidene-2′,3′-dideoxy-α-d-mannopyranosido [2′,3′-k]-1,4,7,10,13,16-hexaoxacyclo-octadecane (3), and (1 R,2 R,7 R,24 R)-3,5,8,11,14,17,20,23,26,28-decaoxatricyclo-[21.4.0.02,7]octacosane (4), the hosts, methyl, 4,6-O-benzylidene-2,3-dideoxy-α-d-mannopyranosido[2,3-b] 1,4,7,10,13,16-hexaoxacyclo-octadecane (2) and 1,4 : 1′,4′ : 3,6 : 3′,6′-tetra-anhydro-2,2′ : 5,5′-bis-O-oxydiethylenedi-d-mannitol (5) have yielded 2 : 1 (guest:host) crystalline complexes with borane ammonia as guest. X-ray analyses of the supramolecular structures of BH3NH3 ·1, (BH3NH3)2 ·2, BH3NH3 ·3, BH3NH3 ·4, and (BH3NH3)2 ·5 have been carried out and BH3NH3 ·1, BH3NH3 ·2, and (BH3NH3)2 ·5 have been shown to reduce acetophenone with enantiomeric excesses of 5, 13, and 10% respectively.

Original languageEnglish (US)
Pages (from-to)355-377
Number of pages23
JournalJournal of Inclusion Phenomena
Volume3
Issue number3
DOIs
StatePublished - Sep 1985

Keywords

  • Chiral crown ethers
  • borane ammonia complexes
  • crystal structures
  • enantioselective reductions
  • glycopyranosides
  • mannitol derivatives

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Chemistry(all)

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