Journal
TETRAHEDRON LETTERS
Volume 45, Issue 35, Pages 6653-6656Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2004.07.009
Keywords
separation tagging; mitsunobu reaction; cyclodextrin
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A new method for separation tagging with cyclodextrin-binding groups is introduced and is exemplified in the context of the Mitsunobu reaction with adamantyl tags. HPLC experiments showed that molecules containing adamantyl groups were especially well retained on Sumichiral OA7500beta-methylated cyclodextrin bonded silica columns relative to many other types of molecules. Two new Mitsunobu reagents, bis-(1-adamantylmethyl) azodicarboxylate (BadMAD) and bis-(2-(1-adamantyl)ethyl) azodicarboxylate (BadEAD), were prepared, used in typical Mitsunobu reactions and separated with both P-methylated cyclodextrin bonded silica and standard silica. (C) 2004 Elsevier Ltd. All rights reserved.
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