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

doi:10.6023/cjoc201805023

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 238-248.DOI: 10.6023/cjoc201805023 Previous Articles Next Articles

Special Issue: 庆祝陈庆云院士九十华诞

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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

陈伟^a, 郭人予^a, 龚建贤^a, 杨震^a,b

a 北京大学深圳研究生院省部共建肿瘤化学基因组学国家重点实验室深圳 518055;
b 北京大学北京分子科学国家重点实验室生物有机分子工程教育部重点实验室北京 100871

收稿日期:2018-05-10 修回日期:2018-09-13 发布日期:2018-09-26
通讯作者: 龚建贤, 杨震 E-mail:zyang@pku.edu.cn;gongjx@pku.edu.cn
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

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

Received:2018-05-10 Revised:2018-09-13 Published:2018-09-26
Contact: 10.6023/cjoc201805023 E-mail:zyang@pku.edu.cn;gongjx@pku.edu.cn
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).

1. Diastereoselective Construction of All-Carbon Quaternary Stereocenters via Intramolecular Oxidative Cross-Coupling Reaction.PDF(5255KB)

Abstract

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.

Key words: oxidative coupling reaction, quaternary stereocenter, tertiary stereocenter, methodology

Cite this article

Chen Wei, Guo Renyu, Gong Jianxian, Yang Zhen. Diastereoselective Construction of All-Carbon Quaternary Stereocenters via Intramolecular Oxidative Cross-Coupling Reaction[J]. Chin. J. Org. Chem., 2019, 39(1): 238-248.

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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

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

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