A new regioselective synthesis of vicinal bromohydrins via free radical decarboxylative bromination of beta-hydroxycarboxylic acids

Diisopropylcarbodiimide-mediated condensations between N-hydroxypyridine-2(1H)-thione and beta-hydroxycarboxylic acids afforded mixed anhydrides which were regioselectively converted into vicinal bromohydrins under neutral conditions.

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Bibliographic Details
Published inSynlett no. 1; pp. 69 - 72
Main Authors Greb, M, Hartung, J
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 05.01.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1,2-bromohydrin
MILD
carbon radical
EPOXIDES
REDUCTION
PRODUCT
stereoselective synthesis
CHEMISTRY
pyridinethione
HALOHYDRINS
REGIO
STEREOSELECTIVE-SYNTHESIS
DERIVATIVES
PRECURSORS
bromination
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Summary:Diisopropylcarbodiimide-mediated condensations between N-hydroxypyridine-2(1H)-thione and beta-hydroxycarboxylic acids afforded mixed anhydrides which were regioselectively converted into vicinal bromohydrins under neutral conditions.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2003-43379