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Reference type: Journal
Authors: Ishii T, Iguchi R, Shinkai S
Article Title: D/L selective re-binding of saccharide-imprinted [60]fullerene-bisadducts based on a saccharide-boronic acid interaction: Development of a molecular imprinting technique useful in a homogeneous system.
Publication date: 1999
Journal: Tetrahedron
Volume: 55
Page numbers: 3883-3892.
DOI: 10.1016/S0040-4020(99)00117-9

Abstract: The memory effect of the D-threitol- or L-threitol-imprinted [60]fullerene-bisadduct [(C-f)-4 or ((f)A)-4], which was obtained from the double addition reaction between [60]fullerene and D- threitol- or L-threitol-boronic acid 1:2 complex (D-1 or L-1), was discussed. In the competitive complexation with D-threitol and L- threitol, (C-f)-4 or ((f)A)-4 diastereoselectively rebound with the original template, D-threitol or L-threitol, respectively, affording the corresponding 1:1 complex [(C-f)-3D or((f)A)-3L]. The selectivities increased with lowering the complexation temperature: under the optimum conditions 48% diastereomeric excess was achieved. (C) 1999 Published by Elsevier Science Ltd. All rights reserved

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