Intramolecular [2+2] Photocycloaddition of Substituted Isoquinolones: Enantioselectivity and Kinetic Resolution Induced by a Chiral Template

被引：44

作者：

Austin, Kerrie A. B. ^{[1
,2
]}

Herdtweck, Eberhardt ^{[1
,2
]}

Bach, Thorsten ^{[1
,2
]}

机构：

[1] Tech Univ Munich, Dept Chem, D-85747 Garching, Germany

[2] Tech Univ Munich, Catalysis Res Ctr, D-85747 Garching, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 36期

关键词：

cycloaddition; enantioselectivity; hydrogen bonds; kinetic resolution; photochemistry; CIRCULARLY-POLARIZED-LIGHT; ELECTRON-DEFICIENT ETHENES; PHOTOCHEMICAL-REACTIONS; ENANTIOMERIC ENRICHMENT; CYCLOADDITIONS; ISOQUINOLIN-1(2H)-ONE; STEREOSELECTIVITY; TRANSFORMATIONS; PHOTOREACTIONS; PRODUCTS;

D O I：

10.1002/anie.201103051

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

From simple to complex: Starting from easily accessible isoquinolones 1 (X=Br, OH), complex cyclobutane photoproducts such as compound 2 can be obtained with high enantioselectivity (88-96% ee) through the use of a chiral template. Compound 3, which was isolated in 53% ee starting from a racemic substrate, is the product of a unique, unprecedented kinetic resolution process. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8416 / 8419

页数：4

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