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通过膦催化 MBH 碳酸酯与色酮的烷氧基烯丙基化反应,实现了无金属条件下 3-烯丙基-2-烷氧基色酮的合成。

Metal-free access to 3-allyl-2-alkoxychromanones via phosphine-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols.

机构信息

Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China.

出版信息

Org Biomol Chem. 2021 Mar 28;19(12):2663-2667. doi: 10.1039/d1ob00215e. Epub 2021 Mar 10.

Abstract

A metal-free access to 3-allyl-2-alkoxychromanones by PPh-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols is described. This reaction is performed under mild conditions and it shows good functional group tolerance, providing a series of functionalized chromanones in moderate to high yields with excellent diastereoselectivities. Deuterium-labeling experiments to probe a possible mechanism and scale-up reaction were also conducted.

摘要

本文描述了一种无金属方法,通过 PPh 催化的 MBH 碳酸酯与色酮的烷氧基烯丙基化反应,将色酮转化为 3-烯丙基-2-烷氧基色满酮。该反应在温和条件下进行,具有良好的官能团耐受性,提供了一系列具有中等至较高收率和优异非对映选择性的官能化色满酮。还进行了氘标记实验以探究可能的反应机制和放大反应。

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