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Atroposelective Synthesis of Axially Chiral 3-Arylindoles by Copper-Catalyzed Asymmetric Cross-Coupling of Indoles with Quinones and Naphthoquinones.
Organic Letters ( IF 5.2 ) Pub Date : 2020-06-17 , DOI: 10.1021/acs.orglett.0c01558
Chao-Chao Xi 1 , Xiao-Jing Zhao 2 , Jin-Miao Tian 2 , Zhi-Min Chen 2 , Kun Zhang 3 , Fu-Min Zhang 1 , Yong-Qiang Tu 1, 2 , Jia-Wei Dong 2
Affiliation  

A copper-catalyzed direct asymmetric coupling of C2 sterically-hindering-group-substituted indoles with quinone and naphthoquinone esters was developed by using the spirocyclic pyrrolidine oxazoline (SPDO) ligand, which was accomplished by metal catalysis for the first time. Diverse structures of axially chiral 3-arylindoles were obtained with good to high enantioselectivities in good to high yields. This protocol can be expanded to implement β-coupling with naphthoquinone esters, providing an alternative way to prepare β-substituted derivatives of both naphthols and naphthoquinones.

中文翻译:

铜催化的吲哚与萘醌和萘醌的不对称交叉偶联,对轴向手性3-Arylindoles进​​行了选择性催化合成。

利用螺环吡咯烷恶唑啉(SPDO)配体开发了铜催化的C2位阻基取代的吲哚与醌和萘醌酯的直接不对称偶联,这是首次通过金属催化实现的。以良好至高的产率获得了具有良好至高对映选择性的轴向手性3-芳基吲哚的不同结构。可以扩展该协议以实现与萘醌酯的β偶联,为制备萘酚和萘醌的β取代衍生物提供了另一种方法。
更新日期:2020-07-02
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