Enantioselective Synthesis of β-Quaternary Carbon-Containing Chromanes and 3,4-Dihydropyrans via Cu-Catalyzed Intramolecular C-O Bond Formation
Enantioselective Synthesis of β-Quaternary Carbon-Containing Chromanes and 3,4-Dihydropyrans via Cu-Catalyzed Intramolecular C-O Bond Formation
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通过 Cu 催化分子内 C-O 键形成对映选择性合成 β-季碳含色满和 3,4-二氢吡喃
DOI：
10.1021/acs.orglett.9b03549
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发表时间：
2019-11-01
期刊：
影响因子：
5.2
通讯作者：
Liu, Wen-Bo
中科院分区：
文献类型：
--
作者：
Cai, Jinhui;Wang, Zhen-Kai;Liu, Wen-Bo
报道了一种铜催化的手性季碳色满和3，4-二氢吡喃的高效对映选择性合成方法。通过手性二甲基环己烷-1，2-二胺配体实现了不对称C-O偶联，并以良好的产率和高对映选择性提供了所需的产物。该方法具有底物范围广，适用于二取代芳基溴和烯基溴。该应用程序是由一个克规模的合成和衍生化的产品对有价值的积木。
A copper-catalyzed efficient enantioselective construction of chiral quaternary carbon-containing chromanes and 3,4-dihydropyrans is reported. The desymmetric C-O coupling is enabled by a chiral dimethylcyclohexane-1,2-diamine ligand and provides the desired products in good yields with high enantioselectivities. This method presents a broad substrate scope and is applicable to diversely substituted aryl bromides and alkenyl bromides. The application is demonstrated by a gram-scale synthesis and derivatization of the products toward valuable building blocks.