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手性铱催化的水相介质中立体选择性和原子经济性的烯基 C-H 烯丙基化/烯基化反应。

Stereoselective and Atom-Economic Alkenyl C-H Allylation/Alkenylation in Aqueous Media by Iridium Catalysis.

机构信息

College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, China.

Department of Stomatology, The Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou 310015, China.

出版信息

J Org Chem. 2020 Jun 5;85(11):7225-7237. doi: 10.1021/acs.joc.0c00619. Epub 2020 May 18.

Abstract

A practical and atom-economic protocol for the stereoselective preparation of various 1,4- and 1,3-diene skeletons through iridium-catalyzed directed olefinic C-H allylation and alkenylation of NH-Ts acrylamides in water was developed. This reaction tolerated a wide scope of substrates under simple reaction conditions and enabled successful gram-scale preparation. Furthermore, an asymmetric variant of this reaction giving enantioenriched 1,4-dienes was achieved employing a chiral diene-iridium complex as the catalyst.

摘要

发展了一种通过铱催化导向烯丙基 C-H 加成和 NH-Ts 丙烯酰胺的烯基化反应,立体选择性地制备各种 1,4-和 1,3-二烯骨架的实用且原子经济性的方法。该反应在简单的反应条件下能容忍广泛的底物范围,并能成功地进行克级制备。此外,使用手性二烯-铱配合物作为催化剂,实现了该反应的不对称变体,得到了对映富集的 1,4-二烯。

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