[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
收藏
页码：12921 / 12924
页数：4
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