240484-80-4Relevant academic research and scientific papers
Convenient synthesis of chiral cyclophanes that can coordinate to metals
Sato, Masayuki,Uehara, Fumiaki,Sato, Kayo,Yamaguchi, Masahiko,Kabuto, Chizuko
, p. 8270 - 8276 (2007/10/03)
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.
