基于分子内交叉氧化偶联反应来非对映选择性构建全碳季碳中心
收稿日期: 2018-05-10
修回日期: 2018-09-13
网络出版日期: 2018-09-26
基金资助
国家自然科学基金（Nos.21772008，21632002）、深圳市科技计划（No.GRCK2017042414425972）、广东省自然科学基金（No.2016A030306011）和青岛海洋科学与技术国家实验室开放基金（No.LMDBKF201703）资助项目.
Diastereoselective Construction of All-Carbon Quaternary Stereocenters via Intramolecular Oxidative Cross-Coupling Reaction
Received date: 2018-05-10
Revised date: 2018-09-13
Online published: 2018-09-26
Supported by
Project 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).
陈伟 , 郭人予 , 龚建贤 , 杨震 . 基于分子内交叉氧化偶联反应来非对映选择性构建全碳季碳中心[J]. 有机化学, 2019 , 39(1) : 238 -248 . DOI: 10.6023/cjoc201805023
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.
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