Synthesis of 5-(hydroxymethyl)pyrrolidin-2-ones by cyclization of amide dianions with epibromohydrin

被引：8
作者：
Freifeld, Ilia
Armbrust, Holger
Langer, Peter
机构：
[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[2] Ernst Moritz Arndt Univ Greifswald, Inst Biochem, D-17487 Greifswald, Germany
[3] Univ Gottingen, Inst Organ Chem, D-37077 Gottingen, Germany
[4] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
来源：
SYNTHESIS-STUTTGART | 2006年 / 11期
关键词：
cyclizations; dianions; epoxides; heterocycles; regioselectivity;
D O I：
10.1055/s-2006-942354
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：1807 / 1810
页数：4
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