Rhodium Catalyzed Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Anhydride

doi:10.6023/cjoc201802004

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

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铑催化酸酐对氧杂苯并降冰片烯的不对称开环反应研究

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

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 E-mail:xujianbin@ruc.edu.cn;adams.bmf@hotmail.com
基金资助:
国家自然科学基金（No.21572198）和云南省应用基础研究计划重点（No.2017FA004）资助项目.

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

Received:2018-02-02 Revised:2018-03-27 Published:2018-04-12
Contact: 10.6023/cjoc201802004 E-mail:xujianbin@ruc.edu.cn;adams.bmf@hotmail.com
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).

1. Rhodium Catalyzed Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Anhydride.PDF(1301KB)

Abstract

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

Cite this article

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]. Chin. J. Org. Chem., 2018, 38(7): 1687-1694.

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铑催化酸酐对氧杂苯并降冰片烯的不对称开环反应研究

Rhodium Catalyzed Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Anhydride

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