Journal
CHIRALITY
Volume 16, Issue 8, Pages 526-533Publisher
WILEY-BLACKWELL
DOI: 10.1002/chir.20069
Keywords
chiral selectors; cyclodextrin derivatives; cyclodextrin dimer; high-intensity ultrasound; molecular mechanics; gas chromatography
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Cyclodextrin (CD) derivatives are important selectors for analytical chiral recognition. Their enantioselectivities and chemical properties depend on ring size and on nature, number and location of substituents. This paper describes the synthesis of 6-O-TBDMS-2,3-O-methyl beta-cyclodextrins bearing in position 2 either a single (R)-Mosher acid moiety or a second CD unit, in view of their possible application as chiral selectors. Most synthetic steps were successfully carried out under high-intensity ultrasound using a new sonochemical reactor developed in the authors' laboratory. 6-O-TBDMS-2-O-methyl-3-[(S)-2-methylbutyl]-beta-CD was also synthesized and tested with gas chromatography; the enantiorecognition power of the other CD derivatives is also being tested. A computational study of model structures to design these CD derivatives. (C) 2004 Wiley-Liss, Inc.
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