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Synthesis 2006(11): 1807-1810  
DOI: 10.1055/s-2006-942354
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 5-(Hydroxymethyl)pyrrolidin-2-ones by Cyclization of Amide Dianions with Epibromohydrin

Ilia Freifelda, Holger Armbrustb, Peter Langer*c,d
a Institut für Biochemie, Universität Greifswald, Soldmannstr. 16, 17487 Greifswald, Germany
b Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany
c Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +381 4986412; e-Mail: peter.langer@uni-rostock.de;
d Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
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Publication History

Received 16 November 2005
Publication Date:
05 May 2006 (online)

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Abstract

The reaction of amide and thioamide dianions with epibromohydrin resulted in regioselective formation of 5-(hydroxy­methyl)pyrrolidin-2-ones (pyroglutaminols) and -thiones. The cyclization of the dianion of N-(2-tert-butylphenyl)acetamide with epibromohydrin afforded racemic axially chiral 1-(2-tert-butyl­phen­yl)-5-(hydroxymethyl)pyrrolidin-2-one with high diastereo­selectivity.

Key words

cyclizations - dianions - epoxides - heterocycles - regio­selectivity

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