Citation: Chen Wei, Guo Renyu, Gong Jianxian, Yang Zhen. Diastereoselective Construction of All-Carbon Quaternary Stereocenters via Intramolecular Oxidative Cross-Coupling Reaction[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 238-248. doi: 10.6023/cjoc201805023 shu

Diastereoselective Construction of All-Carbon Quaternary Stereocenters via Intramolecular Oxidative Cross-Coupling Reaction

Chen Wei ^a ,
Guo Renyu ^a ,
Gong Jianxian ^a,, ,
Yang Zhen ^a,b,,

a.
State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen 518055
b.
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science(BNLMS), Peking University, Beijing 100871

Corresponding author: Gong Jianxian, zyang@pku.edu.cn Yang Zhen, gongjx@pku.edu.cn
Received Date: 10 May 2018
Revised Date: 13 September 2018
Available Online: 26 January 2018
Fund Project: the Natural Science Foundation of Guangdong Province 2016A030306011the National Natural Science Foundation of China 21632002Project supported by the National Natural Science Foundation of China (Nos. 21772008, 21632002), the Shenzhen Science and Technology Project Program (No. GRCK2017042414425972), the Natural Science Foundation of Guangdong Province (No. 2016A030306011) and the Qingdao National Laboratory for Marine Science and Technology (No. LMDBKF201703)the National Natural Science Foundation of China 21772008the Shenzhen Science and Technology Project Program GRCK2017042414425972the Qingdao National Laboratory for Marine Science and Technology LMDBKF201703

Figures(7)

The formation of sterically hindered C—C bond represents a great challenge in modern synthetic organic chemistry. A particularly challenging issue is the construction of all-carbon quaternary stereocenters. Herein, a ceric ammonium nitrate (CAN)-mediated intramolecular oxidative cross-coupling of silyl ethers for direct construction of valuable polycyclic scaffolds is described. The reaction enables sterically congested vicinal all-carbon quaternary and tertiary stereocenters to be installed diastereoselectively. The developed method provides a concise and efficient approach for ligation of two different segments through a compact C—C bond formation, which has potential applications in the synthesis of complex molecules as well as sterically congested natural products.
- oxidative coupling reaction,
- quaternary stereocenter,
- tertiary stereocenter,
- methodology
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