%0 Journal Article %T Synthesis and structure of a chiral areno-bridged [2.4]metacyclophane %+ Saga University [Japon] %+ Chemical Research Division (Bengladesh) %+ Institute of Materials Chemistry and Engineering (Japan) %+ Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF) (LCMCE) %+ University of Hull [United Kingdom] %A Akhter, Thamina %A Islam, Md. Monarul %A Matsumoto, Taisuke %A Tanaka, Junji %A Thuéry, Pierre %A Redshaw, Carl %A Yamato, Takehiko %< avec comité de lecture %@ 0040-4020 %J Tetrahedron %I Elsevier %V 74 %P 329-335 %8 2017-11-29 %D 2017 %R 10.1016/j.tet.2017.11.075 %K Metacyclophane %K McMurry reaction %K Bromination %K Diels–Alder reaction %K chirality %Z Chemical Sciences/Material chemistry %Z Chemical Sciences/Inorganic chemistryJournal articles %X The reductive coupling reaction of 1,4-bis(3-acetyl-5-tert-butyl-2-methoxyphenyl)butane 3 was carried out using TiCl4-Zn in pyridine followed by a McMurry coupling reaction to afford the compounds anti and syn 1,2-dimethyl[2.4]MCP-1-ene 4. Bromination of 4 with BTMA-Br$_3$ in dry CH$_2$Cl$_2$ afforded the interesting compound 1,2-bis-(bromomethyl)-5,15-di-tert-butyl-8,18-dimethoxy[2.4]MCP-1-ene 6 and consecutive debromination with Zn and AcOH in CH2$_C$l$_2$ solution afforded the stable solid 5,15-di-tert-butyl-8,18-dimethoxy-1,2-dimethylene[2.4]MCP 7 in 89% yield. Compound 7 was conveniently employed in a Diels–Alder reaction with dimethyl acetylenedicarboxylate (DMAD) to provide 2-(3′,6′-dihydrobenzo)-5,15-di-tert-butyl-8,18-dimethoxy[2.4]MCP-4′,5′-dimethylcarboxylate 8 in good yield. Diels–Alder adduct 8 was converted into a novel and inherently chiral areno-bridged compound [2.4]MCP 9 by aromatization. The chirality of the two conformers was characterized by circular dichroism (CD) spectra of the separated enantiomer which are perfect mirror images of each other. %G English %2 https://cea.hal.science/cea-01656007/document %2 https://cea.hal.science/cea-01656007/file/Thuery_Tet2017_V0.pdf %L cea-01656007 %U https://cea.hal.science/cea-01656007 %~ CEA %~ CNRS %~ PUBNIMBE %~ INC-CNRS %~ IRAMIS-NIMBE %~ CEA-UPSAY %~ UNIV-PARIS-SACLAY %~ CEA-UPSAY-SACLAY %~ TEST-HALCNRS %~ GS-ENGINEERING %~ IRAMIS %~ GS-CHIMIE %~ GS-PHYSIQUE %~ INSTITUT-SCIENCES-LUMIERE