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

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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