Citation: Hu Jirong, Xu Jianbin, Zou Lingling, Lü Haiping, Fan Ruifeng, Liu Na, Zhou Yongyun, Fan Baomin. Rhodium Catalyzed Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Anhydride[J]. Chinese Journal of Organic Chemistry, ;2018, 38(7): 1687-1694. doi: 10.6023/cjoc201802004 shu

Rhodium Catalyzed Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Anhydride

Hu Jirong ^a ,
Xu Jianbin ^a,, ,
Zou Lingling ^a ,
Lü Haiping ^a ,
Fan Ruifeng ^b ,
Liu Na ^a ,
Zhou Yongyun ^a ,
Fan Baomin ^a,b,,

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

Corresponding author: Xu Jianbin, xujianbin@ruc.edu.cn Fan Baomin, adams.bmf@hotmail.com
Received Date: 2 February 2018
Revised Date: 27 March 2018
Available Online: 12 July 2018
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21572198) and the Applied Basic Research Project of Yunnan Province (No. 2017FA004)the Applied Basic Research Project of Yunnan Province 2017FA004the National Natural Science Foundation of China 21572198

Figures(3)

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).
- rhodium,
- catalysis,
- oxabenzonorbornadiene,
- anhydride,
- asymmetric ring-opening reaction
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