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Separation tagging with cyclodextrin-binding groups: Mitsunobu reactions with bis-(2-(1-adamantyl)ethyl) azodicarboxylate (BadEAD) and bis-(1-adamantylmethyl) azodicarboxylate (BadMAD)

Dandapani, S and Newsome, JJ and Curran, DP (2004) Separation tagging with cyclodextrin-binding groups: Mitsunobu reactions with bis-(2-(1-adamantyl)ethyl) azodicarboxylate (BadEAD) and bis-(1-adamantylmethyl) azodicarboxylate (BadMAD). Tetrahedron Letters, 45 (35). 6653 - 6656. ISSN 0040-4039

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Abstract

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 OA7500 β-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 β-methylated cyclodextrin bonded silica and standard silica. © 2004 Elsevier Ltd. All rights reserved.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Dandapani, S
Newsome, JJ
Curran, DPcurran@pitt.eduCURRAN
Date: 23 August 2004
Date Type: Publication
Journal or Publication Title: Tetrahedron Letters
Volume: 45
Number: 35
Page Range: 6653 - 6656
DOI or Unique Handle: 10.1016/j.tetlet.2004.07.009
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0040-4039
Date Deposited: 17 Oct 2013 15:34
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/19868

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