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一种简便的锆介导的制备芳基化烯丙醇的多组分方法及其在合成高度取代茚和螺茚中的应用。

A facile Zr-mediated multicomponent approach to arylated allylic alcohols and its application to the synthesis of highly substituted indenes and spiroindenes.

作者信息

Guo Shenghai, Liu Yuanhong

机构信息

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032, People's Republic of China.

出版信息

Org Biomol Chem. 2008 Jun 21;6(12):2064-70. doi: 10.1039/b804888f. Epub 2008 May 16.

DOI:10.1039/b804888f
PMID:18528567
Abstract

An efficient and one-pot procedure for the synthesis of arylated and stereodefined allylic alcohols has been achieved through zirconium-mediated multicomponent coupling reactions of alkynes, aldehydes (or ketones), and aryl iodides. The subsequent intramolecular Friedel-Crafts reactions of these allylic alcohols catalyzed by Brønsted or Lewis acids afford highly substituted indenes and spiroindenes under extremely mild reaction conditions. This methodology also provided a highly efficient route to the synthesis of spiroindenepiperidines.

摘要

通过锆介导的炔烃、醛(或酮)和芳基碘的多组分偶联反应,实现了一种高效的一锅法合成芳基化和立体定向的烯丙醇。这些烯丙醇随后在布朗斯特酸或路易斯酸催化下进行分子内傅克反应,在极其温和的反应条件下得到高度取代的茚和螺茚。该方法还为螺茚哌啶的合成提供了一条高效路线。

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