Stereoselective Synthesis of Bicyclo[3.1.1]Heptane Derivatives via Intramolecular Photocycloaddition Reaction
Stereoselective Synthesis of Bicyclo[3.1.1]Heptane Derivatives via Intramolecular Photocycloaddition Reaction
复制标题
分子内光环加成反应立体选择性合成双环[3.1.1]庚烷衍生物
DOI：
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发表时间：
2012
影响因子：
1.8
通讯作者：
S. Inoue
中科院分区：
文献类型：
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作者：
Kiyoshi Honda;M. Konishi;Manabu Kawai;Akihisa Yamada;Y. Takahashi;Y. Hoshino;S. Inoue
α，β，γ，δ-不饱和酯9a和9 c-f经紫外光照射后，分别合成了双环[3.1.1]庚烷环系的1，3-桥环丁烷10和双环[3.2.0]庚烷环系的1，2-桥环丁烷11。在交叉加合物10中观察到在C-6桥接头部的内立体化学的偏好。另一方面，共轭二烯醇9 b的辐射导致通过仅平行环加成到1，2-桥环丁烷11。
Optically active 1,3-bridged cyclobutanes 10 of the bicyclo[3.1.1]heptane ring system and 1,2-bridged cyclobutanes 11 of the bicyclo[3.2.0]heptane ring system were produced by UV irradiation of α,β,γ,δ-unsaturated esters 9a and 9c-f. The preference of endo-stereochemistry at C-6 bridged head was observed in cross-adducts 10. On the other hand, irradiation of conjugated dienol9b led via only parallel cycloaddition to 1,2-bridged cyclobutane 11.