[2+2] Photocycloaddition of 3-Alkenyloxy-2-cycloalkenones: Enantioselective Lewis Acid Catalysis and Ring Expansion

被引：61

作者：

Brimioulle, Richard ^{[1
,2
]}

Bach, Thorsten ^{[1
,2
]}

机构：

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

[2] Tech Univ Munich, CRC, D-85747 Garching, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 47期

关键词：

cycloaddition; enantioselectivity; Lewis acids; photochemistry; ring expansion; FREE-RADICAL FRAGMENTATION; CHARGE-TRANSFER PHENOMENA; INDUCED ELECTRON-TRANSFER; ORGANIC-SYNTHESIS; INTRAMOLECULAR PHOTOCYCLOADDITIONS; PHOTOCHEMICAL CYCLOADDITION; CYCLOBUTANE-FRAGMENTATION; CHIRAL SENSITIZER; NATURAL-PRODUCTS; FORMAL SYNTHESIS;

D O I：

10.1002/anie.201407832

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

By application of substoichiometric amounts (50 mol%) of a chiral Lewis acid, the intramolecular [2+2] photocycloaddition of the title compounds was achieved with high enantioselectivity (up to 94% ee). Upon cleavage of the cyclobutane ring the resulting tricyclic products underwent ring-expansion reactions under acidic conditions and formed anellated seven- or eight-membered-ring systems without racemization. The ring expansion could be combined with a diastereoselective reduction (triethylsilane) or allylation (allyltrimethylsilane) upon BF3 catalysis (48-87% yield).

引用

页码：12921 / 12924

页数：4

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