Asymmetric Bromolactonization Catalyzed by a C3-Symmetric Chiral Trisimidazoline

被引：214

作者：

Murai, Kenichi ^{[1
]}

Matsushita, Tomoyo ^{[1
]}

Nakamura, Akira ^{[1
]}

Fukushima, Shunsuke ^{[1
]}

Shimura, Masato ^{[1
]}

Fujioka, Hiromichi ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 48期

关键词：

asymmetric synthesis; halogenation; imidazolines; lactones; organocatalysis; BRANCHED NONCOVALENT COMPLEXES; ENANTIOSELECTIVE HALOCYCLIZATION; CARBOXYLIC-ACIDS; DESIGN;

D O I：

10.1002/anie.201005409

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A productive alliance: In an enantioselective organocatalytic bromolactonization of 5-substituted hex-5-enoic acids (see scheme), it appears that the formation of an ion pair through interaction of the trisimidazoline catalyst 1 with the substrate both creates a chiral environment and promotes the cyclization by activating the carboxylic acid. DBDMH=1,3-dibromo-5,5- dimethylhydantoin. Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9174 / 9177

页数：4

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