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

Ilia Freifeld; Holger Armbrust; Peter Langer

doi:10.1055/s-2006-942354

PAPER

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

Ilia Freifeld^a, Holger Armbrust^b, 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

Abstract

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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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