TY - JOUR
T1 - The supramolecular structures and reactivities of some complexes of chiral crown ethers with borane ammonia
AU - Shahriari-Zavareh, Hooshang
AU - Stoddart, J. Fraser
AU - Williams, M. Kevin
AU - Allwood, Billy L.
AU - Williams, David J.
PY - 1985/9
Y1 - 1985/9
N2 - 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.
AB - 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.
KW - Chiral crown ethers
KW - borane ammonia complexes
KW - crystal structures
KW - enantioselective reductions
KW - glycopyranosides
KW - mannitol derivatives
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U2 - 10.1007/BF00655736
DO - 10.1007/BF00655736
M3 - Article
AN - SCOPUS:0345309433
VL - 3
SP - 355
EP - 377
JO - Journal of Inclusion Phenomena and Molecular Recognition in Chemistry
JF - Journal of Inclusion Phenomena and Molecular Recognition in Chemistry
SN - 0923-0750
IS - 3
ER -