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Dual C(sp3)-H Functionalization of Cyclic Ethers via Singlet Oxygen-Mediated Ring Opening and Ring Closing.
Yuan, Xu; Yu, Xianglin; He, Kun; Zhang, Ruihan; Xiao, Weilie; Lin, Jun; Zhan, Zhajun; Cheng, Xiaohong; Shao, Zhihui; Jin, Yi.
Affiliation
  • Yuan X; Key Laboratory of Medicinal for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
  • Yu X; Key Laboratory of Medicinal for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
  • He K; Key Laboratory of Medicinal for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
  • Zhang R; Key Laboratory of Medicinal for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
  • Xiao W; Key Laboratory of Medicinal for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
  • Lin J; Key Laboratory of Medicinal for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
  • Zhan Z; College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
  • Cheng X; Key Laboratory of Medicinal for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
  • Shao Z; Key Laboratory of Medicinal for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
  • Jin Y; Key Laboratory of Medicinal for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
Org Lett ; 23(21): 8267-8272, 2021 11 05.
Article in En | MEDLINE | ID: mdl-34633191
A metal-free dual C(sp3)-H bond functionalization of saturated cyclic ethers via photooxidative singlet oxygen-mediated ring opening and ring closing has been developed, providing a method for generating hydrobenzofurans/pyrans/dioxins. Mechanistic studies have confirmed that ring-opening intermediates were effectively generated by singlet oxygen-mediated C(sp3)-H activation and efficiently reacted with aldehydes and activated methylene compounds to form a wide array of products with high diastereoselectivities (up to >95:5 dr). This study is a rare example of α,ß-dual C(sp3)-H bond functionalization of ethers.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2021 Document type: Article Affiliation country: China Country of publication: United States
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2021 Document type: Article Affiliation country: China Country of publication: United States