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 (1R,2R,7R,24R)-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.
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Dedicated to Professor H. M. Powell.
Supplementary Data relating to this article (atomic coordinates of the hydrogen atoms and thermal parameters) are deposited with the British Library as Supplementary Publication No. SUP 82017 (74 pages).
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Shahriari-Zavareh, H., Stoddart, J.F., Williams, M.K. et al. The supramolecular structures and reactivities of some complexes of chiral crown ethers with borane ammonia. Journal of Inclusion Phenomena 3, 355–377 (1985). https://doi.org/10.1007/BF00655736
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DOI: https://doi.org/10.1007/BF00655736