A New Regioselective Synthesis of Vicinal Bromohydrins via Free Radical Decarboxylative Bromination of β-Hydroxycarboxylic Acids

Marco Greb; Jens Hartung

doi:10.1055/s-2003-43379

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Synlett 2004(1): 69-72
DOI: 10.1055/s-2003-43379

LETTER

A New Regioselective Synthesis of Vicinal Bromohydrins via Free Radical Decarboxylative Bromination of β-Hydroxycarboxylic Acids

Marco Greb^a, Jens Hartung*^b
^a Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
^b Fachbereich Chemie, Organische Chemie, Universität Kaiserslautern, Erwin-Schrödinger Straße, 67663 Kaiserslautern, Germany
Fax: +49(631)2053921; e-Mail: hartung@chemie.uni-kl.de;

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Publication History

Received 24 October 2003
Publication Date:
04 December 2003 (online)

Abstract
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Abstract

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

Key words

1,2-bromohydrin - bromination - carbon radical - pyridinethione - stereoselective synthesis

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