Chem. J. Chinese Universities ›› 2010, Vol. 31 ›› Issue (3): 514.

• Articles • Previous Articles     Next Articles

Tandem Synthesis of 1,3-Disubstituted 2,6-Dioxabicylco-[3.2.1]Octane Derivatives

JIN Hui-Juan1,2*, LU Jing1, ZHENG Ning-Juan1, WU Xue1,2   

  1. 1. Department of Chemistry, Yanbian University,
    2. Key Laboratory of Natural Resources of Changbai Mountain & Functional Molecules, Ministry of Education, Yanbian University, Yanji 133002, China
  • Received:2009-03-04 Online:2010-03-10 Published:2010-03-10
  • Contact: JIN Hui-Juan. E-mail: jinhj@ybu.edu.cn
  • Supported by:

    延边大学长白山生物资源与功能分子教育部重点实验室课题基金(批准号: 2009-2011)资助.

Abstract:

A series of 1,3-disubstituted 2,6-dioxabicyclo[3.2.1]octane derivatives were obtained by a tandem reaction of 2-methyl-4-penten-1,2-diol and various aromatic aldehydes catalyzed by indium trichloride in high yields. These products were generated through sequential acetalization, Prins cyclization and intramolecular nucleophilic addition reactions in one pot. All of the new compounds were confirmed via 1H NMR, 13C NMR and MS analysis, and the configuration of product was determined by the NOESY experiment.

Key words: Prins cyclization; Dioxabicyclo[3.2.1]octane; One-pot synthesis

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