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Synthesis of Chiral Sulfonyl Lactones via Copper‐Catalyzed Asymmetric Radical Reaction of DABCO⋅(SO2)
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2018-01-15 , DOI: 10.1002/adsc.201701532
Yang Wang 1 , Lingling Deng 1 , Jie Zhou 2 , Xiaochen Wang 1 , Haibo Mei 1 , Jianlin Han 1 , Yi Pan 1
Affiliation  

In the present work, an asymmetric copper‐catalyzed radical multi‐component cascade reaction of an unsaturated carboxylic acid, aryldiazonium tetrafluoroborate, and DABCO⋅(SO2)2 (DABSO) has been developed for the enantioselective synthesis of sulfonyl lactones. In this reaction, this SO2 surrogate, DABSO was applied for the first time in the construction of chiral compounds. This multiple‐step asymmetric radical reaction was carried out under mild conditions and tolerated a wide range of substrates, resulting in the corresponding sulfonyl lactones with up to 95% chemical yields and 88% ee. The current reaction enriches the research contents of DABSO, and provides a new and efficient strategy to chiral functionalized lactones bearing quarternary stereogenic center.

中文翻译:

铜催化DABCO⋅(SO2)不对称自由基反应合成手性磺酰基内酯

在目前的工作中,已经开发了不饱和羧酸,芳基重氮四氟硼酸酯和DABCO⋅(SO 22(DABSO)的不对称铜催化的自由基多组分级联反应,用于磺酰基内酯的对映选择性合成。在这个反应中,SO 2作为替代,DABSO首次用于手性化合物的构建中。这种多步不对称自由基反应是在温和条件下进行的,可耐受多种底物,得到相应的磺酰基内酯,化学收率高达95%,ee高达88%。该反应丰富了DABSO的研究内容,为手性官能化的具有季生立体中心的内酯提供了新的有效策略。
更新日期:2018-01-15
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