Synthesis of Hexahydro-1H-isoindole Derivatives via Intramolecular Diels-Alder reactions

• Main Authors: Li Yi-Syuan, 李奕璇
• Other Authors: Lin Mei-Huey
• Format: Others
• Language: zh-TW
• Online Access: http://ndltd.ncl.edu.tw/handle/84zc7z

碩士 === 國立彰化師範大學 === 化學系 === 103 === We have been developed a successful synthesis of hexahydro-1H-isoindole derivatives starting from phenacyl bromides. At first, We can get allenol involving indium-mediated allenylation reaction of a phenacyl bromides with propargyl bromide. This process is followed by FeBr3-mediated SN2′-type substitution reaction of the formed homoallenic bromohydrin to produce a 2,5-dibromo-4-aryl-1,3-pentadiene, which then is subjected to a sequential, one-pot Nalkylationreaction with N-allyl-N-(p-tosyl)amine and a highly diastereoselective intramolecular Diels−Alder reaction of the formed ene-diene to generate the target hexahydro-1H-isoindole.