Convenient-synthesis of chiral cyclophanes that can coordinate to metals
Convenient-synthesis of chiral cyclophanes that can coordinate to metals
复制标题
DOI：
10.1021/ja983907u
复制
发表时间：
1999-09-15
影响因子：
15
通讯作者：
Kabuto, C
中科院分区：
文献类型：
--
作者：
Sato, M;Uehara, F;Kabuto, C
Optically pure cyclophanes possessing a 1,3-dicarbonyl moiety were conveniently synthesized from alkanedioyl dichloride in four steps. The intramolecular [4+2]cycloaddition of bis(acylketene)s generated by thermal decomposition of bis(4,6-dioxo-1,3-dioxane) proceeded smoothly, giving cyclophane pyranones in high yields. The compounds possessing 7-10 bridging methylenes were resolved by imine formation with (R)-1-phenylethylamine, followed by basic hydrolysis. These cyclophanes are optically active versions of acetylacetone or salicylaldehyde and formed complexes with metals such as copper and europium. X-ray analysis of the chiral copper complex indicated the pentacoordinated structure of the copper metal with syn configuration of the two bridging chains.
