Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (7): 1687-1694.DOI: 10.6023/cjoc201802004 Previous Articles     Next Articles



胡继荣a, 徐建斌a, 邹玲玲a, 吕海平a, 樊瑞峰b, 刘娜a, 周永云a, 樊保敏a,b   

  1. a 云南民族大学 云南民族大学-香港浸会大学传统天然药物研发联合实验室 昆明 650500;
    b 云南民族大学 民族药资源化学国家民委-教育部重点实验室 昆明 650500
  • 收稿日期:2018-02-02 修回日期:2018-03-27 发布日期:2018-04-12
  • 通讯作者: 徐建斌, 樊保敏;
  • 基金资助:


Rhodium Catalyzed Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Anhydride

Hu Jironga, Xu Jianbina, Zou Linglinga, Lü Haipinga, Fan Ruifengb, Liu Naa, Zhou Yongyuna, Fan Baomina,b   

  1. a Yunnan Minzu University-Hong Kong Baptist University Joint Laboratory of Traditional Natural Medicine, Yunnan Minzu University, Kunming 650500;
    b Key Laboratory of Chemistry in Ethnic Medicinal Resources, Yunnan Minzu University, Kunming 650500
  • Received:2018-02-02 Revised:2018-03-27 Published:2018-04-12
  • Contact: 10.6023/cjoc201802004;
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21572198) and the Applied Basic Research Project of Yunnan Province (No. 2017FA004).

Transition metal catalyzed asymmetric ring-opening reaction (ARO) of oxabenzonorbornadienes is a useful tool in the formation of carbon-carbon bond or carbon-heteroatom bond, which have attracted extensive study and received great achievements over the past decades. A series of efficient catalysts have been established and the high-level control of enantioselectivity for these reactions have been realized. A wide range of nucleophiles including carbon and heteroatom nucleophiles have been used in this reaction. Anhydride is a common acylation reagent and there has been no report about the ARO reaction of oxabenzonorbornadienes with anhydride, which can generate some useful chiral compounds. In this work, Rh-catalyzed ARO of oxabenzonorbornadienes with acetic anhydride and propionic anhydride have been developed. The developed protocol could result in ARO product in high yield (up to 94%) and excellent enantioselectivity (up to 95% ee).

Key words: rhodium, catalysis, oxabenzonorbornadiene, anhydride, asymmetric ring-opening reaction