Chinese Journal of Organic Chemistry >
Rhodium Catalyzed Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Anhydride
Received date: 2018-02-02
Revised date: 2018-03-27
Online published: 2018-04-12
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).
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
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