Enantioselective Lewis Acid Catalysis in Intramolecular [2+2] Photocycloaddition Reactions of Coumarins

被引：118

作者：

Guo, Hao ^{[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, CRC, D-85747 Garching, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 42期

关键词：

chirality; cycloadditions; enantioselectivity; Lewis acids; photochemistry; SUPERCRITICAL CARBON-DIOXIDE; PHOTOCHEMICAL-REACTIONS; ASYMMETRIC PHOTOCHEMISTRY; PHOTODIMERIZATION; STEREOCHEMISTRY; PHOTOADDITION; CYCLOADDITION; CHIRALITY; ALCOHOLS; ALKENES;

D O I：

10.1002/anie.201003619

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Photochemistry goes acidic! In the presence of the chiral Lewis acid catalyst 2 the intramolecular [2+2] photocycloaddition of 4-(alk-4- enyl)coumarins (1) provides the corresponding products 3 with up to four stereogenic centers in a highly chemo-(84-89 % yield) and stereoselective fashion. For R=H, enantioselectivities up to 82 % ee are possible with 50 mol % catalyst 2 and up to 78 % ee with only 20 mol % of catalyst 2. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7782 / 7785

页数：4

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