Cu-Catalyzed asymmetric Friedel–Crafts propargylic alkylation of phenol derivatives,Organic & Biomolecular Chemistry

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Cu-Catalyzed asymmetric Friedel–Crafts propargylic alkylation of phenol derivatives
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-11-06 00:00:00 , DOI: 10.1039/c7ob02133j
Long Shao _{1,

2,

3,

4,

5} , Xiang-Ping Hu _{1,

2,

3,

4}

Affiliation

A copper-catalyzed asymmetric Friedel–Crafts propargylic alkylation of electron-rich phenol derivatives with a variety of propargylic esters has been described. With Cu(OTf)₂ decorated with a chiral tridentate ketimine P,N,N-ligand as the catalyst, asymmetric Friedel–Crafts propargylic alkylation of 3,5-dialkoxyphenol derivatives proceeded smoothly in high yields and with good to excellent enantioselectivities. The present study suggested that the presence of an electron-rich substituent on the meta-position of phenol is essential for the promotion of Friedel–Crafts propargylic alkylation, and the substrate bearing two electron-rich groups on both the 3,5-positions of phenol tends to give a satisfactory performance.

中文翻译：

铜催化苯酚衍生物的不对称Friedel-Crafts炔丙基烷基化

已经描述了铜催化的富电子苯酚衍生物与各种炔丙基酯的不对称Friedel-Crafts炔丙基烷基化反应。用手性三齿酮亚胺酮P，N，N-配体作为催化剂装饰的Cu（OTf）₂，不对称的Friedel-Crafts 3,5-二烷氧基苯酚衍生物的炔丙基烷基化反应顺利进行，收率很高，对映选择性很好。本研究表明，在苯酚的间位上存在一个富电子取代基对于促进Friedel-Crafts炔丙基烷基化是必不可少的，并且底物在两个3,5-位上均带有两个富电子基团苯酚倾向于提供令人满意的性能。

更新日期：2017-11-13

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