title: Synthesis of hexahydro-1H-isoindole derivatives from arylacyl bromides via homoallenic bromohydrins.
abstract: A procedure has been developed for the concise synthesis of hexahydro-1H-isoindole derivatives starting from phenacyl bromides. The approach employs a sequence involving an initial indium-mediated allenylation reaction of an arylacyl bromide 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 N-alkylation reaction 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.
authors: Department of Chemistry, National Changhua University of Education , Changhua, Taiwan 50007.
authors: Mei-Huey
authors: MH
authors: Lin
authors: Yi-Syuan
authors: YS
authors: Li
authors: Chung-Kai
authors: CK
authors: Kuo
authors: Chung-Hao
authors: CH
authors: Chen
authors: Yen-Chih
authors: YC
authors: Huang
authors: Kung-Yu
authors: KY
authors: Liang
authors: Yu-Chun
authors: YC
authors: Chen
authors: Chang-Hsien
authors: CH
authors: Tsai
authors: Tsung-Hsun
authors: TH
authors: Chuang